


What's Ours

by Brenna_Fae, DaydreamDestiel



Category: Supernatural
Genre: Anal Sex, Angst with a Happy Ending, BDSM, Barebacking, Blowjobs, Bondage, Bottom Cas, Bottom Dean, Bottom Jimmy, Butt Plugs, Cas teaches Dean how to Dom, Cockwarming, Comeplay, Dean’s an anal virgin, Dom Castiel, Double Penetration, Edging, Everyone’s 18, Exhibitionism, F/M, Fingering, Fisting, Flogging, Fluff, Frottage, High School, Highschool AU, Homophobic Slurs, Jimmy and Castiel are twins, Jimmy in Panties, Jimmy in a girl’s uniform (for one scene), Kink Exploration, M/M, Masturbating, Polyamory, Private School, Public Sex, Rimming, Sexting, Smut, Sub Jimmy, Super rich Jimmy and Castiel, Switch Dean, Top Cas, Top Dean, Twincest, blindfolding, dcjbb, dcjbb2017, foodplay, handjobs, improvised gag, sex acts on film, vague mention of prior underage sex
Language: English
Status: Completed
Published: 2017-05-13
Updated: 2017-05-13
Packaged: 2018-10-29 04:11:51
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 13
Words: 79,473
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10846218
Author URL: https://archiveofourown.org/users/Brenna_Fae/pseuds/Brenna_Fae, https://archiveofourown.org/users/DaydreamDestiel/pseuds/DaydreamDestiel
Summary: Dean was pissed when Dad landed another new job in another new town that came with a tuition waiver for him and Sam. Just what Dean needed for his last five months of high school school, being surrounded by a bunch of spoiled rich kids he’d have basically nothing in common with. Don’t even get him started on the fact he had to wear a shitty school uniform.When Dean walked into Chemistry on his first day, the last thing he expected was to find himself partnered up with basically the hottest guy he’d ever seen in real life; Castiel Novak. It was way too easy to like Castiel, and Dean was surprised by how quickly he got attached to him.There was just one little kink he hadn’t seen coming: Castiel’s MIA lab-partner was his twin brother Jimmy. Doesn’t seem that bad? Did he mention the whole damn school knew they were together. Yeah, together, together. Which pretty much meant Dean was fucked, and not even remotely in the way he wanted.





	1. Chapter 1

**Notes for the Chapter:**

> Brenna_Fae: Incest is bad right? The reoccurring theme is that Jimmy and Castiel have to hide their relationship and that whatever Dean had would be the 'normal' relationship. So I wondered what would happen if we flipped the script. This was so much fun to write with DaydreamDestiel. As is often the case with us this fic became so much bigger than we expected and it was hard to say goodbye to our boys when we finally finished. My eternal gratitude and love go to DaydreamDestiel for running away with this idea with me and her constant patience and inspiration and thank you to Slunne for the beautiful artwork.
> 
> DaydreamDestiel: This fic was such a pleasure to write. Brenna pitched the idea and started it while I was finishing up some scenes for The Cellist and I was totally hooked from the beginning. I was so worried I'd screw up the absolutely brilliant beginning, but I think we blended pretty seemlessly in the end. ;) So thanks Brenna, for basically babying me through joining in on this, because I know I was needy for a while there. Lol. 
> 
> Thank you to our artist Slunne, who's fantastic art you'll see below. It was great working with you, and we love how the art turned out. <3 
> 
> Check her out on deviantart here: [Slunne](http://slunne.deviantart.com/) and give her some love for her art. :) 
> 
> Thanks to the mods at DCJBB, we had a great time and enjoyed the challenge.

_This fucking sucks,_  Dean thought, as he pulled Baby into a parking spot in an unfamiliar lot.

_Five months, five fucking months, and I woulda been free._

Dean stared at all the faces of strangers talking and laughing and walking in pairs and groups towards the front entrance of the school. His anger boiled up as he took in the building. It was old… and expensive as fuck. Only reason he was even going here was because Dad got free tuition for his kids as a perk of the new job.

The new job. The reason Dean was _here_ and not finishing out the year at the one school he’d managed to start and last more than a couple of months at. Dad had him real fooled that time. Insisted that he’d stick it out at his job at least long enough for Dean to graduate and not have to do the New Kid Dance. _Again._ Yeah fucking right.

It was the closest Dean had come to making good on his threat to drop out and get his GED. But one look at Sammy was all it took to cool his temper enough to drop it. Kid was smart, like _super_ smart. The only deficiency that he had in the brain department was that he looked at Dean like he hung the moon. It wouldn’t matter if Sam knew that it was a bad idea, if Sam hated the idea.

If Dean dropped out then Sam would soon follow. If Dean managed to not fuck up one thing in his life, it would be having any hand at his baby brother reaching his full potential.

Because of that, Dean knew reasonably, that Dad had made the right choice. When the job offer to come work on the fleet of luxury buses for some high end district of private schools in Connecticut came up, John had initially turned it down. Then he found out about the whole free tuition for his kids bit and it was all over. Thanks to that, Dean had to suffer through the next five months so that Sammy could go to a school for rich kids and geniuses.

Didn’t mean he had to like it.

Dean grabbed his bag and pocketed his phone and keys. He just barely managed to stop himself from slamming his car door, no need to take his anger out on Baby. He reached up to adjust the uncomfortable blue tie of the stupid uniform he had to wear before he ran his hand along his leather jacket to ground himself. They’d get _that_ when they pried it outta his cold dead hands.

At least Dean’s mood lightened considerably when a group of lovely young coeds moved around and past him as they walked from the parking lot to the school. He started walking behind them with a smirk and wandering eyes, enjoyed his view very much. Their long legs were accented by grey knee highs, and matching grey plaid skirts. Uniforms did have _some_ perks after all. Could’ve done without the navy blue blazers that partially covered up what Dean was fairly certain would’ve been perky asses, but all in all, it was a damn good look.

Dean quickly forgot his brief moment of happiness at this damn school when he found himself surrounded by snickering assholes in Political Science because the teacher had asked him a question which, Dean assumed by the response, should’ve been easy. But for starters, who the hell asks a kid a question on their first day in a new school.

Second, his last school didn’t even _have_ a Political Science course considering that it was a _normal_ school and not a place like this that wanted to churn out future senators and judges like a little elitist factory. Thankfully, Dean wasn’t so embarrassed that he couldn’t mask it by levelling each one of them, including the teacher, with a nasty glare that had them quieting quickly before moving on.

Calculus was just as bad. Dean managed to not kill anyone by the end of class and felt like he should be rewarded. He planned to take off over lunch and go grab a burger at some greasy diner. Unfortunately, he had to get through one more class. Chemistry, usually a class that Dean actually managed not to hate.

Of course walking into a new classroom and realizing that everyone was already paired up with lab partners kinda sucked. Dean walked up to the teacher at the desk and handed him the same slip of paper with his information that he’d had to do with each instructor. Unlike the others though this one barely acknowledged him. He simply waved Dean off.

“Mr. Novak’s partner is out for the remainder of the week. You can join him until then. We’ll figure something out after that.” The teacher said without even looking up.

Dean scanned the room and landed on the one station that only had one person at it and damn near dropped his bag. Mr. Novak was stunning with dark hair that looked like it was trying to be neat but failing miserably, a strong jaw with a gorgeous cleft chin, lips that were just dying to be kissed and finally piercing blue eyes that...that Dean just realized were watching him curiously as Dean stood there staring.

 _Nice, Winchester, first dude you find hot enough to wanna cross the line from curious to bi for and you look like a complete idiot._ Dean dropped his gaze to the floor and made his way over to the empty seat. He grabbed a notebook and pen out before he dropped his bag and sat, his eyes glued to his notebook. The table was quiet for a few moments as the other students spoke in hushed whisper around him. The silence was broken when Mr. Novak cleared his throat.

“I’m generally more talkative but I prefer to address people by their name and as I’ve yet to learn yours, I feel somewhat awkward.”

Jesus Christ, that voice was doing things to Dean.

“Name’s Dean.” Dean muttered, still looking down, though now it was to hide the flush of his skin.

“Hello Dean. My name is Castiel.”

Dean was so focused on the sound of _that_ voice saying his name that he almost missed the hand that was held up in his peripheral vision. Quickly, Dean wiped his hand on his grey pants to ensure they were free of sweat before he turned and clasped the offered hand. Castiel’s eyes were even more intense up close.

“Sorry your partner’s out and you got stuck with the new kid man. That’s gotta suck. I’ll do my best to hold up my end of the work.” Dean said with a shrug.

Castiel tilted his head and the corner of his mouth curled up in a half smile.

“I’m sure we’ll do just fine, Dean. I imagine it’s not easy getting dropped into a different curriculum. I promise I won’t hold it against you if you don’t know _everything_ right away.” Castiel’s smile grew and his voice filled with affection. “Can’t be worse than my usual partner. He’s a total slacker. Probably wouldn’t even be passing if it wasn’t for me.”

By the end of class Dean was feeling oddly at ease. Castiel was strange, that was for sure. He didn’t get half of Dean’s references, he was quiet one moment then verbose the next, and he was far too serious, didn't smile nearly enough. But damn, when he _did_ smile, it made Dean feel like he’d just aced a test or diagnosed a problem in the Impala before Dad did.

Which is probably how Castiel managed to have Dean wrapped around his finger by the end of class. They’d been dismissed for lunch and they were packing up their bags when Castiel turned and laid one of those smiles on Dean.

“Would you like to join myself and my friends for lunch Dean?”

“Oh… uh… I was actually gonna take off for a bit and grab a burger. You know, take a break from all the strangers and the new kid stares.” Dean stammered as he nearly zipped the skin of his thumb into his bag.

“Oh,” The smile faded from Castiel’s face and Dean felt like he’d just kicked a puppy “I understand. Perhaps another time then.”

Castiel turned to move when Dean’s hand moved of its own volition and he found himself grasping Castiel’s shoulder. With one raised eyebrow, Castiel looked back at him and Dean remembered words would be good.

“That was before I had a friend to hang with though. Sure, I’ll come” Dean said.

“Are we friends then?” Castiel said with another half smile. Dean started to mumble a reply before Castiel took pity on him. “I’m glad. Come on Dean, I’ll introduce you to more friends.”

That was how Dean found himself seated at a table laughing with a bunch of people he’d just met. A far cry from how he’d expected his day to go when he’d first dragged himself out of bed. Castiel’s friends actually seemed pretty cool for a bunch of rich kids. He’d been worried at first.

Castiel had led him over to the table and introduced him before he indicated toward the only other free seat at the table which Dean was happy to see was right next to Castiel. The kids sitting there all seemed to share the same expression that Dean couldn’t quite parse… surprised, annoyed, just plain weirded out? Dean was prepared to stay long enough to be polite and then excuse himself to avoid being looked at like scum on the bottom of someone’s shoe.

But whatever the weirdness was passed and he soon found himself engaged in a heated but friendly debate with a younger Asian kid named Kevin about which was superior, the newer flashier cars or the classics.

“I’m serious, if you can’t pop the hood and fix it yourself without needing a degree in Computer Science then what the hell’s the point? The whole thing’s a conspiracy to make sure people keep buying new cars.” Dean said with a way too animated wave of his hand that nearly caught Castiel in the face.

“Huh, is it really that easy to fix older cars? I figured that since most newer ones just have to be hooked up to a computer to find out what’s wrong that it’d be easier. I mean, that’s what computers _do._ ” Kevin said with a contemplative look.

“Oh yeah man, I mean one look under the hood of a classic and you’ll get it. It’s a different world. Sure you gotta know a little bit but nothing that a little reading and a lot of trial and error won’t get you. But the rest? It’s just… natural… intuitive… you just gotta get to know her and feel it out… listen to her respond.” Dean said with an almost glazed look.

“Dean are you talking about cars or sex?” Castiel’s gravelly voice asked next to him and Dean flushed bright red.

The table was quiet for a beat before every single person save Dean and Castiel burst out laughing. Charlie, the cute little redhead who was wearing a Harry Potter tie pin in defiance of the dress code, gave Dean a playful shove that broke him out of his embarrassment and had him chuckling along with them.

“But seriously man, come with me after school and I’ll let you take a peek under my Baby’s hood… promise she won’t mind.” Dean said with a wink that fed into the joke.

Kevin grimaced as he spoke, “Oh, I’d love to but I gotta catch the bus.”

Guess even when the buses were high end it still sucked to have to ride one.

“Poor little Kev won’t be able to get his license for another year and Mommy and Daddy won’t let him take the limo…  say riding the bus builds character.” Balthazar said and slung arm around Kevin’s shoulder, pulled him into a  headlock and ruffled his hair.

Dean didn’t miss the way Kevin’s cheeks flooded with color or the way he pulled away with a laugh that wasn’t entirely convincing.

“Hey man, I can give you a ride home if you want. If you don’t mind stopping to pick up my little brother.” Dean said as he shoved the last bite of his not entirely awful burger into his mouth.

A dainty hand slid down Dean’s shoulder to rest on his chest and he almost choked when an impressive set of tits pressed into the back of his neck.

“I’d love a ride Dean.” A feminine voice purred in his ear.

“You have your own car, Bela.” Castiel deadpanned from Dean’s side.

Only… was that a note of… possessiveness Dean detected under that careful neutrality? Also, when the hell had Bela vacated her seat. Dean must’ve been really caught up in the conversation.

“Maybe I wasn’t talking about a ride in his car, _Castiel_. Fresh meat looks like he’d be killer in the sack. Sounds like it too if he fucks as well as he takes care of his car.” Bela said as her hand dipped down lower, brushed just below Dean’s navel and caused an involuntary twitch in his pants.

The movement stopped abruptly and Dean looked down. Castiel's fingers tightly gripped Bela’s wrist. Interestingly enough just the sight of Castiel’s hand _near_ Dean’s crotch made his dick jerk even harder.

“Lunch is over, Bela. Time to go to class now.” Castiel said just as neutrally as before.

Bela yanked her hand away and straightened. Dean glanced around and saw the rest of the table were gathering their things and getting up.

“I’ll see you last period, Dean.” Castiel said before he headed off with Charlie and Jo.

Slightly puzzled, Dean dumped his tray and trailed behind Balthazar and Bela, who  spoke to each other in hushed tones.

“...what the hell...”

“...Castiel… weird… playing at…”

“...Jimmy… pissed…”

By the time Dean reached his English Lit class, one that he shared with Bela and Balthazar, evidently, he’d forgotten all about the strange way lunch had ended. He was looking forward to talking cars with Kevin and he was also excited to introduce him to Sam.

The age difference between them wasn’t huge and they were both brainiacs and into some of the same things. Sam could make his own friends, sure, but Dean liked the idea of having someone that might look out for him without Sam having to feel like his big brother was breathing over his shoulder

Dean walked into the the classroom and started for the first available seat. He had to suppress a yelp when a hand reached out and grabbed his arm.

“This way darling, you’re sitting with us.” Balthazar grinned as he pulled Dean to the back and pressed him into a chair situated between him and Bela.

Class was spent enjoying the back and forth snark between Bela and Balthazar, sometimes directed at each other, sometimes at Dean and sometimes about their fellow classmates. Luckily, for once Dean was ahead because the book they were discussing had been covered in the spring semester at his last school so Dean didn’t miss much and even saved his own ass when the teacher got irritated with the threesome and despite the fact that Dean wasn’t even the one doing most of the talking decided to take it out on him.

When Dean answered the teacher’s question without hesitation, he looked annoyed and Bela and Balthazar seemed entirely too pleased. Interestingly, Bela didn’t make another move on Dean the entire time, though Dean was pretty sure that _Balthazar_ was hitting on him in the whole, pull your pigtails kinda way.

In History Castiel was already seated when Dean got there. He quietly slipped into the empty seat next to him and pulled out his textbook and notebook.

“I see you survived class with Bela and Balthazar.” Castiel said drily. “They’re good friends but they can be a bit much in large quantities, especially together.”

“Yeah, can’t say I’ve ever been groped on my first day at any of my other new schools. High marks for this one,” said Dean with a chuckle.

Castiel stared at Dean with an unreadable look before he shook his head, clearly ready for a subject change. Weird.

“Thank you for taking such an interest in Kevin. He’s a great kid but he’s much younger than the rest of us so he often feels out of place I think. We kind of adopted him into the group when he started at the beginning of the year when Balthazar found out he could hack into the school computers without getting caught. We chastised Balthazar endlessly for using him that way but it did little good as I’m sure you can tell.” Castiel said with a shrug and a slight smile that hinted at fondness.

“Anyway, it didn’t take much to figure out Kevin’s motivations for doing it stemmed from loneliness. He’s incredibly bright and excels at his school work, but his parents push him very hard and his social life suffers for it.”

“Hey, it’s no big.” Dean said while he scrubbed at the back of his neck with his hand to hide his flush of embarrassment. “Seems like a good kid. Besides, can’t have him go on thinking that crap about classic cars being inferior.”

“Whatever you say, Dean.” Castiel said with a shake of his head.

Unlike Balthazar and Bela, Castiel proved to be much more attentive to the instructor and both boys remained relatively quiet throughout the rest of class. Dean left Castiel to go to their respective lockers, more than happy to slip into his leather jacket. The teachers might not have been able to convince him to take it off but the heat having been cranked up totally had. Still, the familiar feel and smell of the leather helped Dean to come back into himself after such a confusing day.

Making so many new friends right away after such a rough start was… unexpected. He knew he had Castiel to thank; The others all seemed to look at him as almost a defacto leader so when Castiel chose to bring Dean into the fold, they’d all followed suit. Dean just hoped it would last past Castiel’s need for a lab partner.

Doubts were quickly pushed aside when Dean stepped out of the front entrance of the school and his eyes landed on Baby. He smiled as he took in the people that surrounded her and waited for him. Everyone from lunch was there. Even Balthazar, though he looked like he was attempting some sort of bored affect.

Dean spent about a half hour showing Kevin and a few others the internal workings of his pride and joy. Kevin, as Dean expected, was completely enamored and Dean promised that he would let Kevin know the next time he had to do some work on her so that he could come and watch. Unfortunately Bela started grumbling about being cold and from the shifting of some of the others she wasn’t the only one.

Dean had texted Sam earlier, who’d said he’d hang out in the “insanely huge” library ‘til Dean was done. He sent another to let him know they were on their way. Then Dean said his goodbyes as Kevin slid into the passenger seat. Castiel was the last to go. He lingered long enough to swap phone numbers with Dean, something that Dean was _absolutely_ happy to read more into.

If it lead to him picturing nights of sexting and steamy selfies that let him in on what Castiel had on under his uniform and that ridiculous trench coat that was obstructing Dean’s view as he walked away, who would know?

On the way over to the junior high, Kevin was still full of questions and Dean was only too happy to answer. Still, when Kevin and Sam fell into easy conversation over some video game that they both loved (but Kevin wasn’t supposed to actually play because video games were wasted potential) Dean was a little relieved to have the pressure shifted. He was also beyond thrilled when Sam and Kevin exchanged numbers before Kevin got out and ran into his ridiculously huge house.

Sam moved up to the front and Dean turned the car and headed back in town toward the low rent section. Some of the tension of feeling out of his element lifted as he left behind the neighborhood wealth and status.

“So kiddo,” Dean started as he reached out to ruffle his brother’s shaggy hair. “How was your first day.”

“Good, I guess.” Sam replied, hesitation clear in his voice. “How was yours?”

Dean could tell Sam was bracing himself and he immediately felt guilty. Kid couldn’t even enjoy his new school because he wanted to be like his brother, who was always unhappy in new places.

“It was great, Sammy.” Dean said, and he was surprised to realize he meant it.

“Really?” Sam asked incredulously.

“Really.” Dean said with a smile. “I thinks it's not gonna be half bad here after all. So, tell me all about your new school.”

It was like Dean had given Sam permission to actually like being here and suddenly the floodgates opened. Sam spent the rest of the ride and most of the evening going on about the amazing library, top of the line computer lab, all the brainiac extra curriculars that he wanted to sign up for.

Dad was late getting home as expected but they sat down to a late supper that was unexpectedly relaxed and enjoyable. Dean even got an unusually warm squeeze of appreciation to his shoulder from his dad when Dean assured Sam it would be no problem if he wanted to stay after school for all those things.

The rest of the evening was spent doing homework. There was _so_ much of it to catch up on. But even that wasn’t enough to kill Dean’s good mood and he drifted to sleep with a smile on his lips and blue eyes danced in his dreams.


	2. Chapter 2

Dean woke up in a good a mood for the first time in a long, long, time. Sure he’d gotten used to his last school and even made a few friends but really the biggest selling point for that place had been the fact that the new kid stigma had worn off.

If anything, a change might not be bad since he’d run through enough of the student bodies that it’d started to get harder to find a date. People only cared about how amazing the rumor mill said you were in bed if they thought they had a chance at pinning you down after the great sex.

Of course that line of thinking led to Dean remembering exactly how long it’d been since he got laid as he showered. Which then resulted in soapy, wandering hands that couldn’t resist teasing until Dean was hard, aching.

The hot water was a steady pressure over his shoulders as he propped one forearm against the front wall of the shower, and rested his forehead on it while he slowly fisted himself. He bit down hard on his bottom lip to keep the little sounds that wanted to leak out from being too loud. Felt so good, and Dean couldn’t help but picture Castiel.

 _God,_ those intense blue fucking eyes, full pink lips and perfect goddamn jawline. So hot. He imagined what it’d feel like if Castiel kissed him, brushed those gorgeous lips against his and slipped his tongue hotly into his mouth. _Fuck,_ he bet Castiel was a great kisser, looked like the kind of guy who could take you apart with just his mouth on yours.

Dean’s hand sped up and he pretended it was Castiel’s, thick, long fingers, softer and smoother than Dean’s. He rubbed his thumb over the head of his cock and squeezed a drop of precome from the slit. Pictured Castiel dropping down onto his knees to taste it, eyes wide and looking up at Dean like he couldn’t fucking wait. Dean gasped in a pleasured breath, heat and desire built up in him fast.

Castiel’s lips closed over the tip of Dean’s cock and he smoothed over it in a slow roll of his tongue, right before he sucked Dean down and-

“Shit-” Dean hissed quietly as he came, streaked white over shower wall, and gasped in a choked breath.

Dean’s good mood finally dipped a little as his first classes dragged on and the teacher that had called on him the first day repeated the action. At least this time Dean was able to answer it but that didn’t stop him from glaring at his teacher and getting a scowl in return. But then Chemistry rolled around and Dean was embarrassed to think he might have spent the whole class with a grin on his face.

At lunch Dean was only half paying attention when a snippet of conversation caught his attention, too busy being distracted by the excellent pie that he’d snagged for dessert. At least these fancy schools had pretty damn good food.

“...doing fine, getting spoiled of course.” Castiel said.

“Who’s that?” Dean asked, apologetic at having been caught not paying attention.

“Oh, Jimmy, my MIA lab partner.” Castiel said with an affectionate roll of the eyes.

“Oh yeah, what’s up with him? Why’s he out so long?” Dean asked curiously before he filled his mouth with another bite of flaky pastry.

Castiel laughed quietly as he reached out to brush a bit of pie crust from Dean’s chin. Which Dean forced himself to ignore while he tried very hard to focus on what Castiel was saying instead of the heat that pooled in his belly at such a small touch.

“He had his tonsils out. In truth he probably didn’t need an entire week but Mother and Father dote on him when he’s not well and insisted that he stay home and be waited on.” Castiel said and then tipped the rest of his coffee back.

“Mother and Father?” Dean felt something that had been knotted up inside of him loosen just a bit at the implication of who this lab partner that Castiel had spoken so fondly of was.

“Oh… I thought I mentioned, Jimmy is my brother. My very _spoiled_ brother. He’s got everything in the world to keep him occupied but he complained all evening about being left alone at home.” Castiel said with a shake of his head. “Tried to get me to skip school today.”

“Kid misses you, you know he isn’t used to being without you.” Charlie said with a grin.

“Yes, well that reminds me. I promised to pick him up some gelato from Scalini Fedeli after school, Balthazar. I hope you don’t mind.”

“Really Cassie? That’s in the opposite direction of your house… by almost a half hour.” Balthazar whined.

“I’m aware, but it’s his favorite.” Castiel squinted at Balthazar as he spoke.

“But it’s _Tuesday._ You _know_ that Tuesday is Sophia’s day to work and I only have so long until Margaret and William return home.” Balthazar sounded as if he would be stomping his feet if he were standing.

Dean looked at Castiel with a questioning quirk of his eyebrow.

“Margaret and William would be his parents. He wants to be home before them because Sophia, a lovely young woman who is _paid_ to be in their home to _clean,_ also happens to have schooling in the field of massage therapy.” Castiel explained with a disapproving glare.

“Don’t look at me like that Castiel. If you’d get off your high horse long enough to experience the lovely Sophia’s skills you wouldn’t begrudge me the extremely happy ending.” Balthazar said with a smug tilt of his chin. “Truly Dean, you have to experience it. She works every Tuesday if you’d like to come over for an _unforgettable_ massage.”

Dean couldn’t help but remember his thoughts that morning about the length of his current period of abstinence. He shifted uncomfortably in his seat as he caught Castiel watching and waiting from the corner of his eye.

“Thanks for the offer but I don’t usually have to resort to paying for it.” Dean mumbled without looking up.

The table was silent briefly before laughter erupted at the unintended jab. When it died down Castiel spoke again.

“Really Balthazar, you know I don’t begrudge you a good handjob but this is _Jimmy._ You _know_ how he’ll pout if I come home empty handed. I’d really rather not take a cab all that way. They’ll just take the longest route possible and the gelato will be soup before I get it home. If I’d remembered what day it was I would’ve driven myself.”

“I can take you.” Dean interrupted whatever Balthazar was about to say.

He hadn’t meant to, it just kinda… came out. Castiel glanced at him in surprise.

“Are you… are you sure? It really is quite a bit out of the way. It’ll mean almost an hour and a half of extra travel time.” Castiel sounded unsure.

“Yeah, totally!” Dean suddenly didn’t wanna mention that he also lived a good trek away from the ‘nice’ neighborhood. “My kid brother’s got some after school thing anyway so I was just gonna bum around town ‘til he was finished.”

That was how Dean ended up spending an inordinate amount of time driving around with Castiel. It’d started out a little awkward but when Dean discovered that Castiel was entirely devoid of a decent musical education, he set about going through his cassettes. By the time they pulled into the Junior High parking lot to grab Sam, gelato acquired, Castiel was even humming along to some of the songs he’d indicated taking a liking to which led to Dean replaying them. Of course he wasn’t nearly as loud or as impassioned as Dean was, and Dean fought to keep a grin off his face when he noticed that Castiel was staring at him with a small smile on his lips as Dean sang.

If Kevin’s house was big, Castiel’s house was gargantuan. Dean and Sam both stared with their mouths open as they pulled up to drop Castiel off. Dean wouldn’t be surprised to learn that the house had the same square footage as their high school, maybe more.

Wednesday was fairly uneventful. Dean got to know this new group of friends that he’d acquired through Castiel. The relationship that surprised him the most was the one that he was forming with Charlie. He’d never been great at being friends with girls. Probably his penchant for trying to get in their pants. Something that he never seemed to pick up with guys once Dean had managed to admit that he found them just as bangable.

So maybe it was finding out that Charlie had exactly zero interest in Dean’s dick and never would that allowed him to shake his usual pattern. That and bonding with her over checking out hot chicks and describing in vivid detail what they’d like to do to them in front of the entire table at lunch. It was almost a challenge to see which of them could be more innapropriate, but Charlie had the upper hand since her sweet, sunshiny personality made the filthy things she would say come out of left field.

Thursday started off weird though. Castiel was just walking in when Dean parked. He grabbed his stuff and locked up his car before he made a dash to catch up to him. Only remembered at the last second to slow down and look casual. Castiel just smiled and waved distractedly as they walked into the building together and split off to head to their respective lockers. When Dean got to Chemistry he could definitely tell that something was off.

Whenever Dean spoke, Castiel only gave the barest of acknowledgements. But more than that his entire physicality was different. Castiel was usually calm, grounding, quietly authoritative without even meaning to be.

Now, Dean might even go as far to say that Castiel was disheveled. His clothes were slightly wrinkled like he hadn’t taken his usual care. A glance at his notes showed them to be sparse and scribbled, not his usual neat script. And he wouldn’t Stop. Twitching. His. Damn. Leg.

Seriously, it occasionally jumped so much that it brushed Dean’s and while it was pleasantly distracting it was also… _distracting._ It took everything in Dean not to slam his palm down on Castiel’s knee. Finally Dean couldn’t take it anymore.

“Dude.” Dean hissed in a whisper at Castiel. “What the hell’s going on?”

Castiel looked over at Dean, slightly confused at first, before he slumped in his seat.

“I’m sorry Dean, I’m just a little out of sorts I guess.” Castiel said in a hushed voice as he watched the instructor scribble a formula on the board. “I’m not used to spending so much time away from Jimmy and I guess I’m a little jittery because of it.”

“It’s cool man.” Dean said, then sat back in his seat and fell silent again.

Throughout the rest of class, Dean observed Castiel and as much as he tried, the twitchy behaviour didn’t go away. So when they’d finished packing up their stuff Dean grabbed Castiel’s elbow and started pulling him out of the classroom, through the halls and out the front door.

“Dean, we missed the lunch room by a good deal.” Castiel deadpanned.

“We’re skipping lunch, Cas. You need a distraction and a nice hard ride is just the thing.” Dean said with grin.

“Dean?” Castiel asked, alarm on his face.

“Don’t worry Cas, I’ve got just the girl for you, she’ll take it real easy on you for your first time.”

“Dean!” Castiel finally managed to pull his elbow free and they came to a stop at the edge of the parking lot. “I think I need to make a few things clear. For one, I’m most decidedly _not_ a virgin. Two, I’ve no interest in going to see a prostitute, especially a female one.”

Well that answered that question. Dean pumped his fist in victory… in his head. Outwardly he just smirked and tossed his car keys to Castiel, which he just narrowly caught, before he gestured toward the car they were standing in front of.

“Like I said, Cas. My Baby’s a good girl. She’ll be real gentle.”

Castiel gaped at the keys in his hand, then looked up at Dean.

“Dean, you talk about this car as if she means more to you than life itself. I can’t… why on _earth_ would you let me, a virtual stranger, drive her?”

Dean couldn’t help the happy flutter in his belly. Most people talked about Baby with such disrespect, like she was a thing. Here Castiel was, talking about her properly.

“You’re not a stranger, Cas. We’re friends, right?” Dean asked with a tilt of his head to get Castiel to meet his eyes. “I trust you. ‘Sides, I know where you live and keep all your nice stuff and I haven’t met a house I couldn’t break into when motivated. So Cas? Don’t make me break your stuff, k?”

Castiel swallowed hard, clearly believed Dean, and nodded before he woodenly headed to the driver side door. Dean let out a loud belly laugh, practically doubling over with it, before he made his way to the passenger door.

“Man, I’m just fucking with you. I’ve got insurance and I’m also pretty damn good at fixing her up myself.” Dean slid into the seat once Castiel got in and unlocked his door. “This thing was practically a shell, a beat up one at that, when I got her. Nothin’ you could do to her that I can’t fix.”

Castiel relaxed just a bit and Dean grinned.

It wasn’t until they’d gotten lunch from a drive thru and headed for some winding backroads that Dean finally saw Castiel truly settle. The look of joy on his face as he handled Baby was almost more than Dean could deal with.

They got back to the school and Castiel was flushed and grinning from ear to ear. Dude looked like he’d just gotten laid. Dean couldn’t help but make the correlation out loud.

“Better’n sex, right?” Dean said as he took back the keys when they came together in front of the car to walk back into school.

Dean very much tried to ignore the shock to his system when their fingers brushed. Seriously, what the hell. Castiel was hot but Dean’d never had this kind of reaction to anyone before.

It didn’t help anything when Castiel arched an eyebrow and looked at Dean with the corner of his mouth curled up and Dean would _swear_ his eyes were darker than they were a second ago.

“I think maybe you’ve been having sex with the wrong people Dean. That was very enjoyable but I don’t think I’d go that far.”

It was right on the tip of his tongue, the most obvious comeback: _You offering to show me, Cas?_ Woulda flowed from his lips as naturally as breathing. But instead he stood there a hair too long and the chance passed by as Castiel turned and headed back into the building.

Castiel may have been more relaxed the rest of the day but Dean ended up taking another shower that night… a long one.

Friday it was Dean’s turn to be jittery. He’d been thinking all morning about how long and boring the weekend was gonna be. Dad was gonna take Sam to some museum in Boston so he’d be alone most of it. Plus he was oddly out of sorts over the idea of not seeing someone he’d only just met that week for two whole days.

Dean was quiet all through chemistry. He and Charlie did their, now usual, chick watching thing at lunch. When Balthazar decided to join their little game by pointing out the quarterback of the football team, the entire table seemed surprised that Dean had joined in rather than backing off. He commented on how nice his ass probably looked in his football pants.

“What?” Dean asked defensively, “You trying to tell me that you wouldn’t want a piece of that ass?”

There was another moment’s pause before conversation resumed as normal and Dean didn’t miss the way Castiel tilted his head in that adorable way he did when he was curious about something.

Damn.

Adorable? Really? Dean was so stupidly screwed.

By the end of History Dean had gotten his nerves in check. He was being dumb. There was nothing wrong with asking a friend to hang out. People asked other people to hang out all the time. Didn't have to mean something. Didn't have to be a big deal. Even if it sorta felt like one.

“Hey Cas, my Dad and my brother are ditching me to go to some museum this weekend. Thought maybe you’d, uh, wanna hang out so we can fix your taste in movies, now that we got through music? There’s a movie marathon thing going on downtown with some pretty good flicks. Lasts all day.” Dean asked, tried not to sound too hopeful.

Before he even spoke, Castiel's face answered for him and Dean did his best to push down his disappointment in response to it.

“I’d love to Dean but Jimmy’s been feeling pretty down with being stuck at home alone all week. I promised him I’d spend the weekend with him.” Castiel said though he looked completely torn.

“Hey man it’s cool! I get it. It’s pretty nice that you take care of your brother like that. S’how it is for me too. I take care of Sammy whenever Dad’s busy working or whatever, which is like _all_ the time. Guess our things with our brothers is actually something we’ve got in common.”

Castiel seemed to hesitate briefly, his expression unreadable for a moment, before something akin to understanding flashed across his face. It was there and gone though and Castiel moved on.

“Rain check?” Castiel asked.

“Totally. And I can’t wait to meet your brother. If he’s anything like you I’m sure he’s pretty awesome.” Dean said with a playful shove to Castiel’s shoulder.

Castiel didn’t stop laughing ‘til Dean split off from him and headed to his car and Dean couldn’t even begin to understand why.

***

Dean never thought he’d be so glad to see a weekend in his rearview. It shoulda been a good one. Had the place to himself. Dad’d even gotten him a six pack after he made Dean promise not to leave the house or share it with any of his friends. He didn't mind buying for his son but he wanted nothing to do with other people’s kids.

So Dean spent the weekend eating take out, drinking beer and watching porn in the livingroom. Some people might find it pathetic that he jerked off so many times that he was still a little sore on Monday morning but damn it they didn’t live with a nosey kid brother who didn't understand the concept of knocking. In other words that meant usually the best he could get away with was a quick, uninspired jerk off in the shower.

It _shoulda_ been a good one.

Instead Dean _had_ felt pathetic. Not because of how he spent his time, but because the whole time he couldn’t get over how lonely he felt. Dean resolved to make more of an effort to connect with the rest of the people he was hanging out with so that he could think of more than just one person to call when he wanted to talk to someone.

Speaking of which, Dean couldn’t help his grin when he spotted Castiel where he stood by the steps of the main entrance, one foot propped up on the low wall that ran up the steps as he talked to a few people that Dean didn’t recognize. He was missing his regular trench coat, having traded it out for a heavier peacoat. He’d added a beanie that covered his hair and scarf to it. Dean didn’t blame him. It’d been unseasonably warm but this morning it felt like the temperature had dropped a good twenty degrees.

What surprised Dean were the pink Cons that Castiel was wearing in place of the regulation black shoes. That and he seemed to have picked up a pair of uniform pants that were a size or two too small. Dean bit his tongue as his poor abused dick gave a small throb in his pants. Damn, did Castiel look good in tight pants.

Casually, Dean walked up to the small group and slung an arm around Castiel. In turn, Castiel looked over at Dean with a raised eyebrow and slightly wide eyes. Maybe Dean was being a little more familiar with Castiel than they usually were but _damn_ he missed him.

“Hey Cas, nice shoes. Didn’t think you had it in you, you little rebel.” Dean said with a pat to Castiel’s shoulder.

Castiel’s expression melted into a very relaxed smirk, which, _hey,_ that was new.

“Thanks, man.” Castiel said with a bob of his head.

“I’ll catch you in class, told Kevin I’d meet him before school to talk more ‘bout Baby.” Dean said with a final squeeze before he dropped his arm and walked into the building.

Two classes down for the day, Dean walked into Chemistry and found his world tilting on it’s axis. He at least had the self awareness to _not_ drop his bag but it was a near miss. He _knew for a fact_ that his mouth was hanging open.

Castiel was seated in his usual chair at the lab station. The seat Dean had become accustomed to was also filled. That wasn’t entirely a surprise, he knew Jimmy would be back today. What _hadn’t_ occurred to him, and _why_ exactly it hadn't, Dean had _no_ fucking idea, was that Jimmy would be an almost mirror image of Castiel. How it hadn’t even crossed his mind that two brothers in the same grade would likely be twins was beyond him. He’d just assumed that one of them, probably Castiel, was smart enough to skip a grade. What a _stupid_ mistake to make.

The only difference Dean could really spot was the fact that where Castiel’s hair was short and a little unruly, not for lack of effort, Jimmy’s hair was long enough to almost brush the collar of his regulation dress shirt. Dean waved weakly to Castiel as he walked down the center row toward the back where there was an empty station. He was a little surprised when Castiel’s hand shot out and grabbed his wrist.

“You can still sit with us Dean. You’ll need a partner and at the moment there isn’t anyone else so three will be acceptable.” Castiel said, his eyes serious and… apologetic?

“Yeah Dean, come sit with us. You can have my seat, I’ll just sit in Cassie’s lap.” Jimmy said with a wink.

There it was, that smirk that seemed so uncharacteristic of Castiel earlier. A quick glance down at the two boys shoes confirmed what Dean already knew. Castiel was still wearing regulation black while Jimmy had on baby pink. When he glanced back up Dean could see that Jimmy knew exactly what Dean’d just figured out. The pink of Dean’s cheeks was enough to give it away.

“Or.” Castiel said firmly as he released the wrist that Dean forgot he’d been holding. “He could go get another chair and you and I can slide over to make room.”

Which is exactly what Dean did. Class was… interesting. Jimmy was very talkative. Which was good because Dean was still a little out of sorts and quiet.

He liked Jimmy though. First impressions aside, he was easy in a way Castiel wasn’t. Maybe because Dean felt invested in Castiel already but there wasn’t much on the line with Jimmy? Not that Jimmy wasn’t just as gorgeous as Castiel. More so in some ways, less in others. Dean couldn't help noticing him. A fact that Dean was ashamed to be caught at when Castiel let out a soft chuckle while he watched Dean as Jimmy brought their papers up to the instructor. Well, watched as Dean admired Jimmy’s ass more like. But _damn_ those pants were tight.

Still, there was something about Jimmy and Castiel together. Dean observed it more as he watched them in line at lunch. They’d been late coming, Jimmy had insisted upon a detour on their way there. They finally showed up flushed and in a hurry while everyone else was already sitting with their lunches.

Something about the way Castiel was around Jimmy nagged at the back of Dean's mind. Like Castiel was relaxed, more settled in his own skin.

Dean had been talking with Charlie but evidently he must’ve become distracted because suddenly Charlie nudged him and he realized he had no idea what she’d just said.

“Dean, you with me?” She asked.

“Hmm? Oh yeah.” Dean said, eyes still zeroed in on Castiel as he laughed at something Jimmy said, and a small smile curled up on Dean’s lips. “What were you saying?”

Charlie took a long look at Dean’s face and then followed his gaze. Her smile fell quickly when she realized where he was looking.

“Oh Dean, no.” Charlie said sadly.

Her change in tone got Dean’s attention and he turned toward her in question.

“Tell me you didn’t go develop a _thing_ for _Castiel_.” She pleaded.

A frown crossed Dean's face while he looked down at his tray and shrugged a shoulder.

“Oh sweetie I thought… didn’t anyone tell you?”

“What? I thought… I mean, he didn’t come right out and _say_ it but he kinda implied he was into dudes.” Dean said as he absently dragged his fry through a blob of ketchup.

“Oh no, Castiel is as gay as they come, a firm Kinsey Six. It’s just…” Charlie trailed off before she gestured toward Castiel and Jimmy. “They’re together.”

“Huh?” Dean looked up, completely confused.

“Together, as in: dance at prom, hold each other close, make out 'til you get split up by the chaperones together.”

As if on cue Dean watched Jimmy reach up and tug on Castiel’s tie. He pulled the object of Dean’s desire in and did what Dean’d been wanting to do since the moment he saw Castiel; He leaned in and slotted his lips against Castiel’s. Gave him the most unbrotherly kiss Dean’d ever seen. Dean was sure he saw tongue, and yup, their jaws were definitely moving in a way that suggested there were tongues in mouths that weren’t their own. Dean felt like the bottom just dropped out of his world.

“But… but they’re _brothers_!” Dean hissed.

Charlie grabbing Dean’s arm and hauling him bodily out of his seat only to drag him down the hall toward the bathrooms and out of sight of the table was _not_ what Dean had expected. It _was_ exactly what happened, though.

“Are we gonna have a problem, Dean?” Charlie demanded, fire in her eyes to match her hair.

Dean mentally shook himself and tried to clear his confusion but it wasn’t working. What was _happening?_ Was she suggesting that this was _normal_? Then Dean saw the fight drain out of her and her shoulders sagged.

“I’m sorry. Sometimes I forget… Look, the thing is that Jimmy and Castiel have always been just that… a pair. I guess none of us ever really questioned it. The way those two were growing up it was obvious there would never _be_ any room for someone else.” Charlie’s grip tightened up on Dean’s arm again. “It may not be conventional but I’m telling you right now Dean. Those boys are the sweetest, kindest people you’ll ever meet and every single person in this school loves them. They’ve never done a thing to hurt anyone else and you need to know that if you… if you can’t handle it… you should probably think about not spending as much time around them… or us.”

If Dean thought he couldn’t feel any worse, then he was mistaken. He’d lost any chance he’d with Castiel and now he might lose his new friends too? How had this gotten so twisted around on him?

Charlie finally let go of Dean’s arm and turned to walk back to the table. Dean followed, his head hung low. He sat quietly and forced himself to eat his lunch, ignored the empty seat next to him that Castiel normally would have sat in. Instead he and his brother had taken empty seats on the opposite side of the table.


	3. Chapter 3

Tuesday rolled around and Dean was back to dreading school. He knew he’d been pretty quiet the rest of the day. He’d shrugged off Castiel’s apologetic look when he’d walked into History and of course Jimmy was in the seat Dean’d been using.

Dean had gotten a disturbingly clear picture of the fact that he’d been living in Jimmy’s space while Jimmy had been absent and it sucked harder than Dean expected. Instead he’d flashed Castiel his best smile and no one was the wiser that it faded quickly as he moved to take an empty seat at the back of the classroom.

Maybe he might’ve rushed out of the building and to his car but no one needed to know that he’d sat in the parking lot of the Junior High for an hour while he waited for Sam.

At least by Tuesday morning Dean’d made his peace with the weirdness about the twins being involved. Nothing to do with the fact that when he’d jerked off in the shower it was to visions of twin sets of blue eyes staring intensely up at him as identical mouths mirrored each other while they licked and sucked his cock.

The only real issue now was that Dean was pretty fucking bummed over how he had no chance with Castiel. Even if he _was_ the type to pursue someone already in a relationship it was obvious there was no one coming between those two. At least now it made more sense how out of sorts Castiel’d been without his brother. And it only made Dean feel a tiny bit better that it’d been _him_ that had made Castiel forget himself and smile when he was missing Jimmy.

So fucking petty.

Dean put on his best smile and wore it like a goddamn hair shirt. At least he’d had plenty of practice faking his mood for an audience. He made it through Tuesday and all the way through Wednesday. Dean was even loathe to admit that he was starting to like Jimmy.

He seemed to make an effort to get to know Dean and include him in conversations. He was funny and laid back. Where Castiel’s brand of humor leaned towards wit and sarcasm Jimmy… well Jimmy had a dirty fucking mind that was always firmly in the gutter. That was definitely something Dean could appreciate, even identify with.

Despite that, by the end of the day on Wednesday, Dean was already tired of the facade, even if there had been some genuine smiles and laughs peppered in. So he was a little short with Sam when Sam was running late.

Then at dinner Dean got into a fight with Dad and for once Sam was the one stuck playing referee. So Dean wasn’t terribly surprised to find Sam standing outside his door after Dad had gone to bed.

“‘Sup, Sammy?” Dean asked, left the door open, went back to his bed and flopped down on it.

“Hey Dean… can we talk?” Sam asked softly as he just barely stepped through the door.

Dean gestured silently toward the side of his bed. Sam walked over and sat hesitantly on the edge. They sat quietly for a few beats

“What happened?” Sam asked suddenly, broke the tension.

“What d’you mean Sam?” Dean asked from beneath the crook of the arm he’d draped over his face.

“Things were… things were good for the last week. You were _happy._  I’ve… I haven’t seen you that happy in a new school... _ever_. Then... yesterday you were really quiet and today… well...” Sam let his words trail off.

Dean sighed heavily. He knew he’d been an ass and taken out his misery on his family. They didn’t deserve it. Just ‘cause Dean was unhappy didn’t mean they should suffer. Dad was working his ass off to give them a chance and Sam was doing so well, already wrapped up in school and activities. Something he hadn’t done at any of his other schools because he always had it in the back of his head that it was only temporary. That and Dean knew that if _he_ hated it here then Sam would too, just on principle.

“If you want me to hate it here, I will… “ Sam said softly.

And there it was, spelled out plainly.

“S’nothin Sammy. Just had a bad couple of days. I promise, things are fine.”

They would be.

Time to get outta this funk. Wasn’t like Dean thought Castiel was his _soulmate_ or some shit. He was just a cute guy. There were plenty of other attractive people, Dean just had to let them come to him like they always did.

Fortunately the opportunity presented itself nicely the next day at lunch. Dean’d spent all morning actually _seeing_ the student body now that he wasn’t too busy watching Castiel or thinking about him and it was a damn fine body. More than a few girls were looking his way and even a couple of guys, too. So he was in slightly higher spirits when he got to lunch.

He was surprised when Balthazar came storming into the dining hall and yanked a chair from the table, shoved it away toward another table. Dean watched as he shifted his chair so that there wasn’t enough room for another, spread himself out between Charlie and Kevin. Moments later Bela came stalking in and stood at the door. She glared angrily at Balthazar.

Dean leaned over to Charlie and whispered loudly.

“What’s going on?”

“Oh I’m guessing Balthazar found out that Bela hooked up with Zeke this weekend.”

“I had dibs!” Balthazar shouted in Bela’s direction.

That put Bela in motion and she practically flew toward the table, pointer finger extended and jabbing at the air.

“You _can’t_ call dibs on a _straight_ man, Balthazar.”

“Oh like he would be straight after ten minutes alone with me.” Balthazar scoffed.

“I hate to disagree, Balthazar but Zeke is about as straight as they come.” Charlie said sympathetically.

“See!” Bela shouted, encouraged by the support.

“It’s the principle, darling.” Balthazar sneered.

“Are they gonna be okay?” Dean was once again whispering to Charlie.

“Oh yeah, they’ll be thick as thieves by the end of the day.”

“But not right now.” Balthazar pouted.

“Are you going to get my seat or not?” Bela gave a matching pout.

“No.” Balthazar spat out.

Dean didn’t really think. He just saw an opportunity and he took it.

“You can sit right here, sweetheart.” Dean drawled as he slid his chair back.

He shot his hand out to wrap around Bela’s wrist and gave a gentle but firm tug. She fell giggling into his lap and gave his chest a half hearted slap. Dean was pleased to feel that when she gave a rather intentional wiggle that his dick gave a twitch in interest. He didn’t know why but he was worried that he might be too hung up on Castiel to enjoy anyone else’s company. Clearly that wouldn’t be an issue.

Still, he put his hands on Bela’s hips and held them firmly to still her. No need to be getting up from lunch with an embarrassing tent. Instead he spent the period with Bela practically wrapped around him as they shared Dean’s lunch. He happened to look up once when Bela was whispering something in his ear while she occasionally dragged her tongue along the shell and at the spot just behind it that made Dean fear for the state of his pants.

Castiel was staring at the two of them, his lunch mostly untouched and a spark of anger in his eyes. Probably pissed that he went through all the effort of fending Bela off for Dean that first day only to have the effort be a waste. Oh well, no one asked the guy to save him.

If Castiel didn’t have much to say to Dean the rest of the day, Dean just chalked it up to Jimmy being around to talk to. Didn’t need Dean anymore.

Friday Bela managed to have her own seat but it was pressed as close to Dean’s as physics would allow. Dean was content to sit with an arm slung over her shoulders while his fingers lazily traced the skin along the collar of her regulation dress shirt. A shirt that she wore with several buttons undone which was definitely _not_ regulation but Dean wasn’t gonna complain as his fingers dipped every so often down into the opening. That was just what people could see. Dean was happy to privately enjoy the feeling of Bela’s fingers as they ran lightly up and down his inner thigh, occasionally brushed against the length of his half hard cock, under the cover of the table.

“...you gonna come Dean?” Charlie’s voice drifted across Dean’s hazy thoughts.

“Hmm?” He hummed distractedly.

“Of course he’s coming. He has to buy me dinner at some point if he ever expects me to put out.” Bela purred.

“Oh, so then the hand job you’re giving him now is for the lunch he shared with you yesterday?” Jimmy asked casually before he licked a drip of grease that had come from his burger off of his pinky.

Dean shifted awkwardly, gave himself enough room to drop his arm back down and separate himself a little from Bela and her wandering hand.

“Ouch, so catty Jimmy, what crawled up your ass? Or maybe nothing and that’s the problem?” Bela snarked.

“Oh dearest Bela, if you’d like, I’d happily demonstrate a proper hand job right now. I’m sure Cassie wouldn’t mind.” Jimmy said with a wink, though Dean wasn’t certain if it was directed at him or Bela. “I won’t even make him give me something first.”

Castiel remained silent, though Dean didn’t miss the slight curl of his lips as he continued to be interested in his lunch.

Dean, however, had lost his appetite. He pushed back from the table and grabbed up his bag and tray, then mumbled his goodbyes.

“See you in class Dean, we can talk about tonight then.” Bela called before she returned her glare to Jimmy.

Several hours later Dean was freshly showered and shaved as he stood in front of his mirror and inspected his outfit. It’d occurred to him while he was dressing that this was the first time he’d be around his friends outside of school and the uniform they all had to wear. He’d panicked briefly while he imagined them all wearing expensive designer clothes.

It didn’t last though. Dean looked damn good and he knew it, even going simple with a tight black tee that hugged the smooth muscles of his chest, shoulders and arms, ripped jeans that fit snuggly around his ass and hips and heavy worn biker boots that gave him just an edge of danger when paired with his smooth as butter leather jacket.

Happy with what he saw, Dean was turning to grab his jacket from the bed when there was a soft knock on the door.

“Come in.” He called as he slipped into his jacket and plucked his wallet, keys and phone from the dresser.

He’d been expecting Sam so when he turned and saw Dad there, Dean was surprised.

“Hey Dad, what’s up? I was just about to head out.” Dean said, tried not to let his nerves slip into his voice.

“Yeah, Sam said you had a date.” Dad said softly.

“Look Dad, I know you’re beat and wanna head to bed but Sammy’ll be fine. There’s frozen pizza and Sammy said he’d be fine with cooking it for you guys and-”

“Dean, it’s fine. I’m glad you’re going out. It’s Friday night, you _should_ be going out.” Dad said firmly before his voice softened. “I know you’ve had to take the brunt of dealing with Sam and missed out on a lot of things you should be doing. He’s getting older though and he can manage taking care of himself once in awhile and now that I’ve got a job with steadier hours… well… I know it’s a little late but maybe I can get back to the job of bein’ a dad.”

“I know you’ve done your best, Dad. You know I love that kid and I’m happy to keep an eye on him.” Dean said as he shifted uncomfortably. He wasn’t used to this kind of open discussion with his father, feelings not being either of their forte.

“Yeah well, speaking of bein’ a dad...” Dad reached into his pocket and pulled out his wallet, plucked several twenties from it before he shoved them into Dean’s hand. “I’m sure wherever you guys are going ain’t gonna be cheap. Those kids have probably never been to a Denny’s in their lives.”

“Dad no, this is too much.”

“Just take it Dean, think of it as back payment for all the babysitting you’ve done over the years. Might pay it off in oh, a decade or so.” Dad said with a good natured clap to Dean’s shoulder before he turned around and left.

Dean stood there a little stunned for a moment. He contemplated the likelihood that aliens had kidnapped his father and replaced him with a double. With a heaving breath he shook his head clear and left for his date. More likely that this move had been good for him. Sam too. All the more reason for Dean to make it work.

When Dean pulled up to Bela’s house he wasn’t surprised to see that it was just as big as Kevin’s, though not nearly as big as Jimmy and Castiel’s. Dean was beginning to get the picture that in this town there was rich and there was Novak rich. For a fleeting moment Dean wondered if that was why everyone was so willing to ignore the whole incest thing but Dean quickly shook the thought away. Jimmy and Castiel really _were_ good people, kind and considerate, and it was clear that they were happy with each other so anyone that cared about them would want that for them regardless.

Dean was just getting out of his car to go up to the door when it flew open and Bela ran out, heels and coat in hand. Stunned, Dean stared as she bolted down the drive and practically threw herself into the car.

“Let’s go Dean!” She called from her side when Dean still stood half in, half out of the car.

Honestly, Dean wasn’t surprised that Bela was in a hurry. He doubted any parent would let their daughter out dressed like Bela was with a blouse that was so thin that Dean could clearly make out the fact that she wasn’t wearing a bra and a skirt that barely skimmed her thighs just below the v of her legs. It was so short that as Bela had been running Dean was pretty certain that he could tell that a bra wasn’t the only underwear she didn't have on.

Quickly, Dean slid behind the wheel. Grinned as he adjusted himself before he turned the keys and threw the car into drive. He was looking forward to finding out.

When they pulled up to the place Bela directed him to Dean looked at it with a raised eyebrow. Guess Dad didn’t really need to worry about the cost. He glanced over to Bela and back to the seedy looking bar.

“Really?” Dean finally asked.

“Don’t be so judgey, Dean. We like to go slumming sometimes. It’s exciting, you’ll see.” Bela said wisely.

By the skin of his teeth, Dean managed to bite his tongue as he walked around to open Bela’s door and escorted her inside. Really wasn't hard to spot the group of teens after they walked through the doors. They might’ve dressed down but they radiated a general out of placeness that was obvious by the glances of the other patrons.

“You’ll have to slip the bouncer a fifty. I’m all paid up.” Bela whispered as the gruff looking man approached them. “I’m just going to go powder my nose darling.” She said louder before she headed off in the direction he assumed the bathroom was.

Dean just shook his head and pulled out his wallet. He handed his fake ID over to the bouncer who looked like he was about to say something before he actually looked at it. Probably thought it was gonna be a crappy fake and that he’d get to shake Dean down, but Dean didn’t mess around with this shit. He was handed back his ID and then Dean headed over to the bar, noted that the group at the table already had drinks in front of them.

“Well hey there handsome,” drawled an older, but still very attractive woman who stood behind the bar polishing glasses. “What the hell you doin’ with that crowd?”

She must’ve recognized Bela when they walked in together. Dean wondered how often they came to this place.

“That obvious, huh?” Dean asked with a grin.

“Sweetie, they can buy the most expensive cheap clothes they can find but it still ain’t gonna wash the stink of money off ‘em. You ain’t got that though. Not to mention it ain’t hard to spot leather that’s been worn smooth from years of use over leather that was bought that way.” She said, leaning forward onto the bar while exposing her considerable assets over the spill of her own leather top. “What can I get you?”

“Umm, whatever she usually gets.” Dean said with a gesture toward where Bela had disappeared to, “And a shot of jack and a beer, whatever’s cheap and cold.”

Dean watched as she poured a glass of white wine before she grabbed a bottle of beer from the fridge behind her. Next she slapped a shot glass down on the bar and poured an even pull from the bottle of Jack. She glanced up at him then over at the table before she poured again, made it a double.

“That one’s on the house darlin’.” She said.

Dean laughed.

“They aren’t so bad, just maybe a little disconnected from the rest of the world. Can’t be blamed for what they’re born to any more’n we can.”

The woman poured herself a shot and tipped it toward Dean who followed suit.

“I’ll drink to that.”

Dean was just downing his double when he felt a hand slide up his back beneath his jacket. He looked over at Bela who was giving a look to the bartender that had Dean grabbing their drinks and spinning towards the table. To her credit, the bartender didn’t take offense, instead chose to let out a bawdy laugh before she went back to polishing glasses.

The group made room for them and Bela neatly slid into Dean’s lap after he sat which made it all too easy for him to rest a hand on her thigh and run his thumb along her skin, just barely slipped up under the fabric of her skirt. It provided a good distraction because he didn’t really want to think about how good Jimmy and Castiel looked. And since when did he start caring how Jimmy looked anyway?

Unfortunately even Bela could only distract him so long. It was entirely impossible to ignore Jimmy when he wore black jeans that looked painted on, a bright blue henley that just made his eyes pop even more and an expensive looking imitation of a surplus navy field jacket. His longer hair curled around his popped collar, and Dean hard a hard time not staring because he looked fucking hot.

And Castiel looked every damn bit as good sitting beside him in dark wash jeans, a grey t-shirt and open black cardigan that did nothing to hide the subtle definition in his chest and arms. If it was hard not to stare at Jimmy, then it was a fucking miracle Dean managed to look away from Castiel at all.

He also couldn’t help but notice that while Castiel and Jimmy were sitting next to each other they seemed to be keeping the PDA to a minimum. For some reason Dean had expected them to be all over each other with as much that they did at school. Clearly though, they were aware enough of their situation to know that not everyone in the outside world was gonna be cool with two obvious siblings being intimate. Wasn’t the same as if it was someone like him and Sam that looked nothing alike… and didn’t _that_ kill any possible boner he might have been working toward.

He shifted in his seat uncomfortably before he gently slid Bela off his lap and stood.

“I’m gonna go grab a table, anyone wanna play?” Dean asked as he started to walk toward the pool tables.

He was surprised when a hand wrapped around his wrist and he looked back to see Jimmy holding him firmly.

“They aren’t exactly into sharing the tables with us, Dean.” Jimmy said as he eyed the people around the tables warily.

“Aww, sweetheart.” Dean purred, the Jack and beer loosening him up just enough to not care that he probably shouldn’t say shit like that. “S’just cause you haven’t asked ‘em right.”

Dean looked over at the tables again to make sure none of them were looking his way before he pulled his hand from Jimmy’s grasp. He grabbed his beer and dumped a little on his fingers, splashed it on his face and hand before wiping them clean on his pants.

The group stared at him as he sauntered over to the tables, picked the one nearest that had a couple of rough thirty something looking guys playing. The older ones tended to be less gullible and more likely to look past the surface and the younger ones tended to be too cautious with strangers. As he neared and drew their attention he made sure to add a subtle little stumble, not so much to look campy but enough to imply he may have had a few too many.

“Hey guys!” Dean said a little too loudly and enthusiastically as he took a cue down from the rack on the wall, struggled a bit with pulling it down. “Mind if I play too?”

Both men took him in, briefly considering before they looked back to where Dean had come from. Clearly they weren’t as good at reading people as the bartender cause they took one look at the table watching them and laughed meanly.

“Fuck off back to your little friends. While you’re at it why don’t you send the slut in the skirt over? _She_ can handle my pool stick if she wants.” The guy said lewdly.

Dean assumed he was talking about Bela since Charlie was tucked away in the corner of the booth but it didn’t matter. He had to grit his teeth and grip the cue to keep from cracking it over the dude’s head, just glad that his friends couldn’t hear anything. Bela might not be a prude but no one needed to talk about his friends that way.

“C’mon man…. I know! I’ll play you for the table!” Dean said like this brilliant idea had just occurred to him. “If I beat you, then we get the table for the rest of the night.”

“Yeah and what do I get when I beat _you?_ I’ve already got the table.” He asked with a roll of his eyes directed towards his buddy.

Dean got out his wallet and pulled out the cash there, squinted at it as if he was trying to count it and was having trouble. He tossed the money to the table, gave the appearance of giving up on counting it.

“Whatever’s there. You get that _if_ you beat me.” Dean said cockily, before he swayed a little.

The men eyed the money on the table. There was at least a hundred there. Still, they hesitated. Dean didn’t have any more money to throw in though and for a moment he thought he was out of luck. Then he felt a warm slim hand rest on his shoulder.

“You boys throw in another hundred to go with the table and I’ll throw in a blow job from the _slut_.” Bela purred from Dean’s side. Apparently the voices had travelled.

“Deal.” The douche said as he eyed Bela hungrily before Dean could say otherwise.

Dude musta had a thing for barely legal cause even dressed as she was Bela didn’t look a day over her age of eighteen. Only made Dean want to pummel him even more. Money was tossed onto the table to join Dean’s which Bela gathered up. She walked past Dean towards the high table next to where they were playing and whispered as she passed.

“I hope you know what you’re doing Dean.”

If Dean wasn’t certain of what was going to happen he might’ve been nervous about the added pressure. Not that he’d let Bela make good even on the off chance he did lose. Can’t collect on a blow job if you’re unconscious.

Dean watched as the two men set about racking the balls before the one not playing sauntered over to stand next to Bela. Dean wasn’t about to let it distract him though, Bela would let him know if she needed a hand.

Dean leaned down and lined up to break. He looked up at douche number one and flashed him a smug wink before making the break, sinking four balls without even looking away from him. The color drained from the guy’s face as he watched Dean take stripes and sink every single one with ease before he called his last shot and sunk the eight ball.

Bela came bouncing over with a squeal of delight as the ball dropped. She slipped the cash into Dean’s pocket before she wrapped her arms around his neck and pulled him down for a long, slick, warm kiss. Dean didn’t take his eyes off the guy as he kissed her back, watched as he started toward Dean before his buddy put a restraining arm out and they left to go find a table to sulk at. When they’d gone Dean let himself actually enjoy the kiss, his own hands sliding down to cup Bela’s ass.

When he happened to catch sight of the table, he realized they were all still watching, though it was too dark to read their expressions at this distance.

“C’mon guys,” Dean said loudly with a laugh. “Let’s play some pool!”

They all moved to take over the high tables around the pool table. First game ended up being girls versus boys, Charlie and Bela versus Dean and Balthazar. Balthazar put up quite a fuss when Bela insisted she didn’t know how to play and Dean had to teach her. Charlie, to her credit, just rolled her eyes at Bela’s antics. 

But Dean was competitive, so he told her she’d have to manage on her own. Then he watched as she leaned over the table much further than breaking required and he let loose a loud groan. Her skirt slid up just a little bit more as she leaned. And damn it, Dean was right about the underwear. From the way Bela wiggled, she was well aware that she was showing the _entire_ bar from the edge of the tables over, the curve of her bare ass, the dip between her cheeks all the way down to just the start of her slit.

Dean didn’t have to look, but he did anyway, and he saw the assholes from earlier had their eyes glued to what Bela was serving up. Dean pushed away from the wall he’d been leaning against and moved swiftly up behind her, pressing against her as he reached forward and slid his hands down her arms to guide her hands along the pool stick.

“I guess I’ll have to show you how to play after all.” Dean said. “I don’t think you’re used to playing with the big boys.”

“I think I can handle you, Dean.” Bela said with a snort.

“Wasn’t talkin’ bout me sweetheart.” He growled.

As if on cue Dean heard a warning called out from one of his friends seconds before a hand grasped his shoulder and pulled him back then shoved him aside. He was completely unsurprised to find the two men he’d hustled standing there, a mix of anger and lust in their eyes, always a dangerous combination,

“C’mon guys, we won the table fair and square. I don’t want any trouble.” Dean said while he swapped the cue he’d pulled from Bela’s hand to his left hand and raised his right in mock surrender.

“Fair my ass. You cheated.” Douche number one said as he poked Dean roughly in the chest.

“It ain’t cheatin’ if you make a dumb assumption.” Dean gritted out, tried to keep from escalating things but felt a simmer of anger build in his gut nonetheless.

“You know what, you can keep the table, asshole. But I want somethin for my money you _stole_. I think I’ll take that blow job I was cheated outta.” Douche One reached out to grab Bela, who for the first time actually seemed to be taking in the seriousness of the situation.

Dean was quicker though.

His hand shot out lightning fast and before the guy could even register it Dean had ahold of his arm and had it twisted roughly behind the guy’s back, the pool stick he pressed across his throat forced him back against Dean.

“Bad idea pal. The lady’s _clearly_ here with me. Even if she wasn’t I don’t recall her inviting you to put your hands on her.” Dean said low and dangerous next to the guy’s ear.

“She invited the whole damn bar by flashin’ her goddamn pussy like the slut she is.” He managed to respond before Dean pressed the cue into his windpipe and effectively cut off his air.

“I don’t fucking care if she walked in the bar buckass naked. That’s her prerogative and she _still_ gets to say who can and can’t put their grubby fingers on her. Welcome to the goddamn twenty first century you little prick.” Dean finished, emphasised his point by putting more pressure on the arm he held, just this side of breaking something.

Then Dean let the guy go in one quick move, stepped back to ensure he didn’t get a sucker punch in. The guy was too busy bent over double as he tried to draw in a breath.

“I suggest you take your buddy home before he goes and does something stupid and gets himself hurt.” Dean addressed the other guy, who up ‘til now had been practically unacknowledged.

Dumb jerk hadn’t even made a move to help his friend out when Dean had ahold of him.

Dean watched as the coward nodded and grabbed his friend’s arm, dragged him out of the bar, and only stopped long enough to throw cash on their table to cover their tab. When he was sure they were gone, Dean turned back to face the table. All of his friends were staring silently at him, mouths somewhat agape.

“Anyone wanna play some pool?” He asked, the grin on his face not quite enough to erase the darkness in his eyes.

“Fuck that was hot.” Balthazar said, finally broke their silence.

“He’s right!” Charlie piped up. “I’m gayer’n Christmas and I’d do him right now!”

“Yes, yes it was.” Bela agreed breathlessly.

Dean had just enough time to toss his pool stick to the nearest person, Castiel as it happened, before Bela pulled on his arm and dragged him away.

“For the record, you’ve got an open invitation to put your grubby fingers wherever you want whenever you want.” Bela said as she pulled him into the dim back room that served as a waiting area for the bathrooms.

“Is that a fact?” Dean asked with a grin before he backed Bela against the nearest wall.

That was all the talking there was room for because Dean leaned in and pressed his lips to Bela’s. Quick and hot, he slipped his tongue into her mouth, brushed it along hers before he sucked her bottom lip into his mouth. Nipped at it a little roughly, but judging by the way Bela arched against him she liked it that way.

When Dean’s fingers dropped down and started a slow slide up Bela’s inner thigh she moaned into Dean’s mouth and parted her legs just a little. Dean took up the invitation and let his fingers continue on their path up her skin until they met with soft, wet warmth. He teased at her slit with his pointer finger a little until Bela whined softly. Then he dipped in and gently circled her clit. When her legs started to shake he dropped his free arm down to wrap around her waist tightly, held her up.

“Jesus Bela, you’re already so fucking wet and so close.” Dean groaned as he moved to suck and lick at her neck.

“God Dean, I practically came right there on the spot. People-” Bela gasped as Dean’s finger slid down and pressed inside her. “People usually figure that I get what I deserve if I put it out there.”

Dean pumped his finger a couple of times before sliding his middle finger in along with it. He went back to circling her clit, this time with his thumb, while he slowly fucked her. By then, Dean was supporting her full weight, her legs basically useless. The second he felt her walls start to tighten around his fingers and her cries grew louder, Dean picked up his pace. He gave one final hard suck at the skin over Bela’s pulse and she fell apart on him, his hand slicked up further as she shook through her orgrasm.

When she was done, sated and loose against him, her breathing slowed back to normal, Dean carefully slipped his fingers out and tugged her skirt back down with his clean hand.

“Why don’t you go clean up and I’ll walk you back to the table, sweetheart.” Dean said before he brushed a gentle kiss across her swollen lips.

Bela smiled and walked over toward the bathroom. As Dean turned to watch her go, his eyes fell on a figure standing just inside the doorway. Jimmy. He gave a noncommittal wave to Bela as she walked by but didn’t take his eyes off Dean.

 _“Jesus Jimmy,_ how long have you been there?” Dean asked as color rose in his cheeks.

“Long enough.” Jimmy said with a shrug.

Then he walked over to Dean with a purpose and Dean backed up, unsure why, until he found himself pressed into the far corner of the small room.

“Long enough to see Bela left you high and dry.” Jimmy said as he crowded into Dean’s personal space.

Dean froze in place when Jimmy grabbed the hand that he’d just had buried in Bela and started licking off all the glistening wetness, slipping both fingers into his mouth before he sucked hard.

Dean was so distracted while Jimmy practically went down on his fingers that it took a minute for him to even realize that Jimmy had used his free hand to open Dean’s jeans up and had pulled his painfully hard cock through the opening of his boxers. One of Dean’s hands came up to press against Jimmy’s shoulder ready to push him away and his other hand pulled loose of Jimmy’s grasp to wrap around Jimmy’s wrist, intended to stop the slow and _painfully_ good handjob that he’d started without Dean’s knowledge.

“Jimmy, what the fuck are you doing man?” Dean gasped, weakly pressed his hand against Jimmy without any real conviction.

And then Jimmy’s hand stilled at the light pressure, so Dean dropped his hands entirely, knew he should stop this but really didn’t want to. With a smirk, Jimmy’s hand resumed it’s torturous speed.

“What am I doing? I would’ve thought that was obvious Dean. By the way you made Bela come with just a few fingers I figured you had experience. Was I wrong Dean? Has no one ever jacked this beautiful cock for you before?” Jimmy said with a fairly evil grin before he leaned in to whisper, hand never stilling or speeding up, “Are you a virgin, Dean?”

“Yes! No! I mean… Yes, I’ve gotten a fucking hand job before. No, I’m not a fucking virgin.” Dean said around gasps, his eyes squeezed shut. Felt so good he couldn’t keep them open, but he focused through the pleasure enough to get out, “Cas… what about Cas?”

“Cas?” Jimmy asked, "You mean the guy that's been completely despondent and hiding it from everyone but me since he found out you were going out with her?"

"I don't understand..." Dean started as he forced his eyes open.

"See, Cassie, he asks for so little… wants so little for himself. I'm the needy bottom in this relationship.” Jimmy said, accented it with a flick of his wrist that had Dean weak in the knees. “So when my brother wants something enough to admit it… well it's my job to make sure he _gets it_."

With one last twist and a press of Jimmy’s thumb just below the swollen head of Dean’s cock in exactly the right spot, Dean came hard, sagged against Jimmy as he caught Dean’s spend in his hand.

After a moment, when Dean stopped shaking Jimmy took a step back and Dean watched wide-eyed as Jimmy proceeded to lick his hand clean before he turned away with a grin.

A second’s hesitation passed before Dean tucked himself back into his boxers, did up his jeans and followed Jimmy back to their friends on weak legs.

He felt pretty damn low when he spotted Bela standing next to Balthazar and he realized he’d completely forgotten about her. She must have come out and seen everything. He thought she'd be mad but when she caught his eye she simply shrugged and smiled.

Then Dean only had eyes for Jimmy and Castiel. Jimmy had found Castiel tucked in behind where Balthazar and Bela stood watching Charlie take her shot. Fascinated, Dean watched as Jimmy leaned in to whisper something to Castiel before he kissed him deeply, mostly hidden behind their friends.

Dean had come close enough that he heard it when Castiel moaned into the kiss and Dean knew without a doubt that it was because Jimmy had told him that he’d just licked up all of Dean's come and now Castiel was practically getting off on the taste of Dean in Jimmy's mouth.

Holy _shit_ was Dean ever totally and completely fucked.


	4. Chapter 4

Dean didn’t know what the fuck to do.

He spent the whole weekend jacked up on nervous energy. Checked his phone every ten goddamn minutes, even slept with it next to his head in case something came in late at night or really early. He didn’t hear a word from Castiel. Kevin texted him once to ask about some obscure german car from the fifties. Bela had texted to thank him for the good time. And still _nothing_ from Castiel.

Dean was so worked up that by the end of the weekend he had himself nearly convinced he’d dreamed up the whole thing. That he’d come home after getting Bela off and was so hard up that he’d dreamed about getting jacked.

Would believe it too if the damn little moan that Castiel had made wasn’t echoing in his head every moment of the fucking day, way too perfect to not be real.

When he did stop long enough to let himself actually think he couldn’t figure out what the hell he actually wanted. For fuck's sake, he didn’t even know what was being _offered_.

Did Castiel just want a quick fuck? Hell, sounded good to Dean but for the first time he wasn’t sure if that was _all_ he wanted. Or was Jimmy talkin’ about some threesome shit. Sure, Dean’d had his little fantasy jerk off session but was he really cool getting down and dirty with a couple of brothers?

That was another thing that wasn’t helping. Dean hadn’t gotten off since Jimmy jerked him off in the back of the bar. He tried, but as soon as he started picturing blue eyes and plump pink lips, his thoughts got all jumbled and just… generally fucked up.

When Monday came around Dean was in a mood. He wasn’t angry like he’d been last week so Sam didn’t comment on it as Dean dropped him off before he headed over to the high school. He was… quiet. Couldn’t get out of his own head. Mostly he was trying to figure out what the hell he was supposed to say to Castiel and Jimmy. That and he wondered if word had spread about what Bela had witnessed.

Dean just… needed a little more time to think. Sounded stupid since he’d done nothing _but_ think about it. Still, Dean was glad he wouldn’t see anyone for a few more periods.

Of course as soon as he pulled into a parking space he spotted Balthazar, Jimmy and Castiel standing near the entrance huddled together and laughing. Something dark inside Dean told him they were laughing about _him_ , that they were waiting to ambush him and tell him it was all just some prank, some new kid hazing shit.

Realistically, Dean knew it wasn’t true. It hadn’t taken long for him to see that none of them were like that, even Jimmy who he’d only known a couple of days.

Still, as Dean neared the school, Castiel looked up, saw him and Dean’s stomach clenched. He lifted a hand to wave and looked like he was gonna say something but then Dean just lifted his own hand and waved back before he hurried past into the building.

For once his first two classes flew right by. Before he knew it he was standing in the doorway of his Chemistry class. Jimmy and Castiel were already in their seats but they hadn’t noticed him yet, a fact Dean was grateful for as he stared at the empty chair at their station. He was about to make himself walk over when he felt a firm hand land on his shoulder.

“Mister Winchester, good.” Dean started as both Jimmy and Castiel looked up when their instructor said Dean’s name. “Miss Sands’ lab partner is out today so you’ll be partnering with her.”

Dean masked his rush of relief with a weak smile and shrug toward the twins as he walked over to an empty seat next to Josie Sands. This time he couldn’t ignore the disappointed slump of Castiel’s shoulders and it twisted at that dirty dark feeling in him something awful. He hated that look but it wasn't like he _chose_ not to sit with them.

Class was over way too quickly and Dean knew his last momentary reprieve was over. There was no avoiding lunch unless he wanted to make a point. So Dean bit the bullet and scooped up his bag. Went and stood by the door.

With a deep breath, he turned and waited for Jimmy and Castiel as they gathered their things. Dean noticed that Castiel perked up a little when he saw that Dean was waiting for them and some of the tightness he was feeling let up.

He could do this. It was just a walk down the hall and then lunch with a group of people. Totally normal. Something Dean kept chanting in his head as they walked and the dining hall doors came into view.

Then suddenly Dean felt hands on his back and he was pushed through the the bathroom door to his left.

“Hey, what the hell?!” Dean exclaimed as he narrowly avoided tripping over his own feet.

He spun around and watched as Jimmy and Castiel filed in behind him. Angrily, he’d been about to ask Jimmy what the fuck he thought he was doing, ‘cause it’d clearly been Jimmy that’d just shoved him in here judging by the tense shoulders and firm set of his jaw, when a toilet flushed.

Some kid Dean didn’t recognized walked out and started washing his hands before he noticed the other people in the room.

“Hey Jimmy, Cas.” The guy said with a smile and a wave.

“Hey man, we need the room.” Jimmy responded apologetically.

“No problem, catch you later.” Said the kid and with no further argument he dried off his hands and walked out.

Of course he didn’t argue. Because everyone loved Jimmy and Castiel and would give them everything and anything. Dean was the goddamn freak in this scenario.

Uncomfortably, Dean watched as Jimmy walked along the bathroom stalls, pushed each one open, before he returned to the door and turned the lock. Dean swallowed hard before he backed up and leaned against a sink. He suddenly needed a little support.

“What’s up guys?” He asked, his voice not quite as steady as he would have liked.

“Really Dean, _that’s_ what you’re going with? Ignorance? It doesn’t suit you, you’re too smart for that.” Jimmy said dryly.

“Jimmy.” Warned Castiel softly, though he still refused to look directly at Dean.

“No, Cassie. No ‘Jimmy’. _I_ did this, _I’m_ the one that forced the issue. So if Dean’s gonna be an asshole to anyone it better be me, not _you_.” Jimmy growled out.

“What the hell are you talking about Jimmy? I haven’t done anything to either of you!” Dean said as he pushed himself back up to standing.

“Exactly. You’ve been giving Cassie the brush off, ignoring him this morning, not saying a word to him in class. He doesn’t _deserve_ that Dean.” Jimmy spat out, clearly pissed.

“Jimmy, stop. This isn’t-”

“What the fuck do you guys want from me?” Dean interrupted. “Like, I don’t have any fucking clue what to do here.”

“Dean-” Castiel started, but Dean kept going, the flood gates had broken open.

“I mean, you wanna fuck Cas? Let’s do it. You know I’m into you. Though, I woulda made more of an effort to hide it if I’d… but yeah, c’mon. I can be Jimmy’s little present for you. You wanna do it here? I mean, depending on what you want we can make it work. Didn’t bring any lube to school, so you might have to settle for a blow job. I’m not really into the whole spit for lube thing.”

“Dean-” This time it was Jimmy that tried to interrupt while Castiel stood there silent and slack jawed, his cheeks flushed a pretty pink.

Dean didn’t miss the tent in his pants though, not even a little.

“Or heck, let’s ditch. There’s a crappy little motel near that bar. You guys like to slum, right? Swing by the store, pick up some lube and a whole big box of condoms. I’m gonna need a little more to go on though, I mean. Jimmy says he’s the bottom so I _assume_ you’re gonna wanna top? Me, pretty sure I’m a switch so I’m good with whichever but a little heads up. Also, how’s it gonna work with you two? I mean, I’m _assuming_ Jimmy’ll be there, you guys are pretty inseparable, save major surgery. But like, are you gonna watch, we both gonna have a go at Cas, or were you thinking you're gonna lay me out and spitroast me? I’m gonna have to draw the line at DP. Sounds fun but my ass hasn’t seen enough action to be near loose enough for that.”

“Jesus _fuck_ Dean do you ever just _shut the fuck up_?” Castiel’s voice rang out loud and echoed off the walls of the bathroom.

For a moment both Jimmy and Dean stood there and stared at him. Dean was pretty sure he’d never even heard Castiel swear before.

“God, what the hell was I thinking. The two of you together is gonna give me _such_ a migraine.” Castiel said as he rubbed his temple. “ _Neither_ of you ever stop talking long enough to bother _listening.”_

After another beat, Dean did his best to relax his body so he looked less like he was getting ready to swing into fight or flight mode. He leaned back against the sink and raised his hands to gesture.

“Okay Cas, I’m listening.” He said softly, gave Castiel his full attention.

“This… this isn’t how things were supposed to go. Jimmy… he gets a little _over eager_ when he gets something in his head. He told me what he said to you. Yes, I was a little… unhappy… to see you dating Bela. I don’t have anything against her. Quite the opposite, I actually adore the little pain in the butt. I was just frustrated, I guess, to see her touching what I wished was mine.”

“Cas-” Dean said as his confusion grew.

“We’re _listening_ right now Dean.” Castiel said firmly, with a look that had Dean’s mouth snapped shut. “Of course I told Jimmy all about you the day I met you. We don’t keep anything from each other, ever. Naturally he was intrigued and couldn’t wait to meet you. When I mentioned you’d wanted to get together over the weekend and I turned you down he was… displeased.”

“Pissed, I was pissed, Cassie, it’s okay, if you can say fuck you can say pissed.” Jimmy said while he rolled his eyes.

Castiel sighed and squeezed his eyes shut against Jimmy’s interruption before he continued on.

“He thought it would have been a good opportunity to meet you and gauge your reaction but I felt a more organic meeting was in order. When I noticed you spent a good deal of time watching Jimmy and I when we were being intimate I had hoped that maybe… but then you directed your attentions toward Bela and I assumed you had lost interest. I was… unhappy, but I understood.”

“Despondent, you were fucking despondent. I said it before and I’ll say it again.” Jimmy muttered.

“Fine, I was _despondent_. So Jimmy, out of love, decided to take matters into his own hands… literally as it were.” Castiel seemed to finish, a fond smile curled the corner of his mouth as he looked at Jimmy.

“Okay, so great. You think I’m hot, you know I think you’re hot. I’ve… I’ve told you I’m down with whatever… told you what I’ve got to offer. What’s the problem?” Dean shifted uneasily against the cold porcelain.

“Is that really all you have to offer? All you want? Sex?” Castiel asked quietly, not meeting Dean’s eyes.

“What the hell else is there Cas? Pretty obvious that you’re taken.” Dean responded frustratedly.

Jimmy’s snort had Dean looking his way warily.

“Dean. C’mon. We’re brothers that fuck. Do you really think that we’d be all that hung up on societal norms like monogamy?” Jimmy said with a grin.

“You know I hate it when you boil what he have down to just ‘fucking’, Jimmy.” Castiel said crossly.

“Yeah yeah, I know.” Jimmy said before he hooked an arm around Castiel’s neck and tugged him down to brush a soft kiss against the crown of his head.

Dean couldn’t help but envy the way the tension drained from Castiel at Jimmy’s touch. He stood silently and watched as Castiel collected himself. Dean had no clue where this was going. None whatsoever.

“What I’m proposing is that we date.” Castiel finally said.

“Date? Like you, me, dinner and a movie, home by ten?” Dean asked as he tried desperately to catch up.

“And Jimmy.” Castiel corrected.

“Huh?” Dean asked, still back on the ‘let’s date even though I’m in a committed loving relationship with my brother’ thing.

“You, me and Jimmy, dinner and a movie. Home by… well that’s negotiable but I’ll be sure to ask your parental figure when your curfew is.” Castiel said.

“Wait, so all three of us, cozied up in a booth at some restaurant?” Dean asked, not really sure about the idea of feeling like a third wheel.

“I mean… that’s negotiable too, I really don’t _have_ to-” Jimmy started uncomfortably, likely misunderstanding Dean’s hesitation as not being interested in him.

“No Jimmy, it’s the both of us or neither. That’s the deal. It’s what we’ve always said and that isn’t going to change.” Castiel said as his hand lifted to grip at the arm still draped over him.

Dean stood there a moment while he tried to cycle through all the reasons this idea was bad with a capital B but couldn’t seem to form coherent thought as two sets of cerulean blue eyes bored into him.

“Anyone ever tell you, you shouldn’t make someone feel like they’re standing in front of a firing squad when you ask ‘em out?” Dean barked out.

Jimmy and Castiel both seemed to become aware that they were in fact staring and shifted awkwardly, looked anywhere _but_ at Dean which was actually worse.

“Shit.” Dean swore as he scrubbed his hand through his hair. “Sure. Yeah. Why not? Let’s do this.”

“Really?” Jimmy asked, clearly surprised at how easily Dean gave in.

Castiel, for his part, looked at Dean like he’d had all the faith in the world that Dean would choose correctly.

“Yeah, really. There’s just one thing.” Dean said before he strode toward the twins, both of them tensed up at his approach.

He placed a hand on each of their shoulders before he leaned in to Castiel, pressed his lips gently against Castiel’s and swept the seam with just the tip of his tongue. Just a quick thing before he pulled back and gave Jimmy’s mouth the same treatment. Then, as the twins stood there slightly stunned at the sudden turn in Dean’s demeanor he leaned between them to whisper in both their ears.

“Just didn’t sit well that there were two people out there walkin’ ‘round that knew the taste of my come but I hadn’t had so much as a taste of ‘em.”

With that Dean pushed between them and turned the lock on the door. He was a little surprised that the kid from before was standing outside the door watching people walk by. At least that explained why no one had come pounding on the door.

More relaxed than he’d felt in a while, Dean headed toward the dining hall and gave a small grin when he looked behind him at Jimmy and Castiel as they scrambled to follow. He couldn’t help but be a little pleased that they’d been the ones to get flustered this time.

Lunch… was interesting.

Of course, Dean and the twins were the last to the table because they’d been otherwise occupied. Still, there were the same two empty chairs together and another empty one at the other side of the table left for Dean. But when he moved to sit there Jimmy beat Dean to the table, set his tray down and grabbed the chair.

Then he pulled it over, nudged their two empty chairs apart, just barely the width of another chair. Dean couldn’t help but blush when Jimmy indicated with a nod that he was waiting for Dean to move in front of the chair he held.

It only deepened when he did so and Jimmy smoothly slid the chair up behind him so he could sit in it. The embarrassment at being treated like the ‘girl’ in Dean’s eyes was quickly lost to warmth when Jimmy and Castiel took their places on either side of him, both pressed against him much the way Dean and Bela had been before.

It was so comforting in fact, that Dean didn’t even really think twice when he was finished eating and leaned back to drape an arm over each of them. If confused looks were traded amongst the rest of the group, no one voiced anything at all.

By Thursday, Dean had just barely started to relax into his new role as Castiel and Jimmy’s plus one. Adjusting to the fact that he was allowed to touch them, kiss them, was equal parts awesome and nerve wracking. Each time he did it, he felt like a kid stealing candy or something. Like he was gonna get caught even if there was no one to _catch_ him.

The thing that kinda surprised Dean, though, was how much he enjoyed it; the casual way they touched him. Didn’t even have to be remotely sexual, just a little brush of hands or the way they stood just a fraction of an inch closer than personal space would normally allow for, and warmth would suffuse Dean’s chest.

Dean _liked_ being with the twins, not just because they were smokin’ hot either. They were both smart, for one, even if Jimmy acted like he wasn’t a lot of the time. He was still way smarter than he gave himself credit for. And for two, they were adorable with each other, Castiel indulged Jimmy and Dean thought it was way too cute.

Same time though, sometimes Dean wondered what the hell they saw in him. Because it seemed to him that Jimmy and Castiel were perfectly happy together. But then Castiel would give him one of those smiles that made his heart beat dangerously fast, or Jimmy would give him that little smirk that made Dean’s cock jerk in his pants and he’d forget all about it. _He_ sure as hell wasn’t gonna question his luck. 

It might’ve seemed to someone on the outside, like things were moving pretty fast and Dean was falling pretty hard, and they’d sort of be right. Because Dean already felt gone on them. Between seeing them at school, and the way they texted him well into the evening each night, it felt like they’d known each other a lot longer than they actually did.

Especially when Dean considered the fact that he’d only known Jimmy for a week and change. Add in that they hadn’t had time to really see each other outside of school? And yeah, it was definitely fast. Did group texts even count toward real life relationship stuff?

Dean had no fucking clue. He figured Jimmy and Castiel really didn’t either because as far as he’d gathered, they’d never done this before. So, it sort of felt like waiting for the other shoe to drop, because, if none of them had ever done it, Dean couldn’t really be sure it would work out.

Still, texting with the two of them in the evenings had definitely been interesting to say the least. Even via text Jimmy and Castiel had distinctively different voices. Castiel texted them random memes he found amusing, and asked questions like ‘if you could do anything with your life what would it be?’ whereas Jimmy texted them what was probably an unhealthy number of snapchats he’d saved to text them with hysterical quotes.

Once in awhile Jimmy would throw in a question like ‘Comeplay, yes or no?’ or ‘Hair pulling, are you a fan?’ which Dean seemed to be the only one who answered, half-hard just because Jimmy’d asked a question. Castiel always followed up Dean’s answer with ‘/Jimmy/’. Dean figured the slashes were for emphasis so Jimmy could tell even in text that Castiel was using that, you-will-obey-me tone of voice on him.

Half the time Dean had to excuse himself from the conversation for a few minutes so that he could jerk off right the fuck then, because he’d already been half-hard, and even just reading about Cas using that tone got him ready to go in record time. He could pretty much hear it in his head, and then that’d lead to all sorts of fantasies. Castiel telling Jimmy what to do, or telling Dean what to do, or Dean’s personal favorite; telling Jimmy what to do _to_ Dean.

Then he’d finish and sleepy-hazy Dean would wonder if the two of them were in the same room while they all texted. It was kinda cute to picture them cuddled up in bed texting him, but at the same time it made him a little jealous and lonely. He still had a hell of a time wrapping his brain around the whole being interested in more than one person at a time thing.

It was like, society told you that when you loved someone, you wouldn’t be tempted by anyone else and if you were then you weren’t in love with that person in the first place. Jimmy and Castiel though, were clearly in love. Anyone with eyes could see that.

And yet, they’d both told Dean they wanted him, and yeah, okay, at first maybe Dean thought Jimmy was just going along with it for Castiel, but as they’d gotten to know each other a bit better, they’d been clicking together too, so maybe no so much? 

“...Dean?” Castiel asked while he squeezed Dean’s knee gently to get his attention.

Dean’s brain snapped back to the conversation he was having with Castiel. He looked up from their table in Chemistry and found Castiel concerned and Jimmy faintly amused, “Hmm?”

“I was just saying that if you’re free Saturday, Jimmy and I would like to take you on a date.” Castiel said, almost stiffly, like he’d been rehearsing it, and judging by the way Jimmy’s smirk widened he definitely had.

Dean grinned, “Yeah, sure, Cas.”

Castiel smiled back at him and Dean just suddenly thought that whatever happened, he wanted to keep putting that look on Castiel’s face, “Great! We’ll need you all day Saturday though, where we’re taking you is a bit of a drive, and the activity we’ve planned will take up the whole day anyway. We’d probably return fairly late as well. If your father doesn’t mind.”

“I’m sure he’ll be fine with it. He’s got the day off, so he’ll be around to watch Sammy. ‘S all good. Am I allowed to know where we’re going?”

“Nope!” Jimmy interjected, “It’s a surprise.”

Dean’s eyebrow raised, “So, what should I wear then?”

Jimmy grinned and Dean just knew something dirty was about to come out of his mouth, but Castiel cut him off, “Just something comfortable. We’ll take care of the details.”

Amused, Dean smirked at Jimmy’s pout, before he shifted uncomfortably. He felt kinda weird about them planning whatever the hell they were planning. Like it oughta be his job to plan the date even though that was ridiculous because he certainly hadn’t planned the little ‘date’ he’d gone on with Bela. Then again, that’d been less of a date and more of a group outing and-

And Dean was getting caught up in his head again and he was positive Castiel had just asked him a question but he hadn’t heard a damn word of it, “Uh?”

Castiel’s head tilted just a little to the side, “I said we’ll leave fairly early on Saturday. Jimmy and I will pick you up if you text us your-”

Dean’s mild panic at the idea of them picking him up was cut short when Jimmy let out a little whine of.. frustration? 

“Why can’t we just leave late and stay overnight? You know I hate waking up early on the weekend.” Jimmy complained.

“I thought we agreed we were dating Dean, not just having sex with him.” Castiel argued, reasonably. “You don’t have a sleepover on the first date, Jimmy.”

“Hey, maybe Dean _likes_ sleepovers on the first date, how would you know?” Jimmy countered.

Dean’s eyebrows rose, what the fuck, “Dean’s sitting right here guys.”

They both had the grace to blush faintly at his comment, which Dean really liked.

“Sorry.” They both muttered then glared briefly at each other before Dean’s laugh startled them out of it.

“How ‘bout a compromise?” Dean suggested, glad for an excellent excuse. “I’ll drive over to your place for nine so you won't have to come pick me up, that way Jimmy can sleep in a bit. Then I’ll drive myself home after.”

Jimmy lit up at the suggestion, but Castiel seemed to consider it before he finally agreed, “Alright, but we’re taking our car to the date.”

“That work for you, Jimmy?”

“Well, it’s better than the ass-crack of dawn, Cassie wanted.” Jimmy said with a shrug. “I still think we should just stay over in the-”

_“Jimmy.”_

“Alright, fine.”

“If it makes you feel better, I gotta be home Sunday morning. Dad’s got weekends off now and he says Sundays we all gotta have breakfast together like a real family or whatever. It’s lame, but kinda nice, I guess.” Dean said with a little flush because he definitely hadn’t meant to reveal that much, “Plus I told Sam after breakfast I’d give him a ride to Kevin’s before I come work on our Chemistry project with you guys.”

“Sam? Who’s Sam?” Jimmy asked.

“Jimmy, I told you Dean had a younger brother.” Castiel said distractedly as he  measured out some blue chemical they were supposed to mix with a yellow chemical that was somehow supposed to turn clear instead of green if they did it right.

“Oh yeah! When do I get to meet him? He as hot as _my_ brother?” Jimmy asked with a ridiculous waggle of his eyebrows.

“He’s _thirteen_.” Dean answered, narrowing his eyes down at Jimmy. “And isn’t that a touch narcissistic of you to say about Cas?”

For his part, Jimmy just shrugged, unaffected by Dean’s death glare.

“Sure but I ‘spose you’ve gotta be at least a little bit to fuck your mirror on the regular.”

“Jimmy!” Hissed Castiel, just as he accidentally dumped the entire contents of the yellow beaker into the blue which caused an entirely different reaction that ended with Castiel and Dean mopping up the foamy remnants while Jimmy laughed himself to tears.

Dean was glad for the distraction though because for about half a second he’d wondered how the hell he was gonna tell _his_ brother that he was so okay with the idea of two brothers screwing that he was willing to get in on the action himself.

The rest of class passed pretty quickly and while Dean didn’t stop thinking about what Jimmy and Castiel were planning, he learned pretty quickly that neither of them was going to slip up with carefully posed questions.

Randomly throughout Thursday and Friday Dean tried to imagine what exactly they would be doing on Saturday. Honestly though, he had no damn clue what they might plan that’d take a whole day and be a long drive away.

Bedtime on Friday night Dean had to push down a flash of excitement so he could get some sleep. Whatever it was, Castiel had said _activity_ which meant actually _doing_ something, so Dean should really get some rest so he didn’t make a total idiot of himself in front of them. Especially if it was something that required coordination. What if it was something he didn’t know how to do? Wow, what if he sucked at whatever it was? Shit.

 _Fuck off,_ Dean told himself, _if I don’t get some freakin’ sleep I’ll_ definitely _fuck something up._


	5. Chapter 5

Saturday morning came fast. The kind of morning where Dean needed a coffee before he could even contemplate functioning properly. Luckily the caffeine perked him right up, so he wasn’t too worried about keeping up with Castiel and Jimmy. A quick shower, toast with peanut butter, mandatory last minute teeth brushing and Dean rushed out the door with a quick _see ya later_ tossed over his shoulder to Dad and Sam.

Far as they knew, he was going out with some new friends from school for the day and wouldn’t be back until late. He _still_ hadn’t told Sam about Jimmy and Castiel. He told himself he just hadn’t had time, but truth was every time he’d had a second he’d found another reason to put it off. Realistically, he could’ve made time, made a moment, but he still hadn’t worked out exactly how to say he was dating not just one guy but two… who were twins…

Sure, Sam knew Dean was sort of into guys too, who else was Dean supposed to confide in when they kept having to move? Not like he had any close friends. Basically his choices for discussing major life crises was Sam or Dad. And yeah, no contest there. He loved Dad, don’t get him wrong, but considering he was pretty much the reason that Dean only _had_ two choices to pick from and both were family? Yeah, Sam it was.

But there was a big difference between your brother being theoretically bi, and him dating twins. And even if it was kinda dumb, Sam’s opinion of him meant a lot to Dean. He didn’t wanna fuck it up. Sam would understand though, Dean knew, he always did. It was just a matter of getting his brain to get his mouth to open the fuck up and say what needed to be said.

Tomorrow. Or maybe Monday… or next weekend maybe he’d take Sam out for burgers and… yeah. But soon. Definitely wasn’t gonna put it off indefinitely. Totally _not_ gonna do that.

Dean started up the car and drove to Jimmy and Castiel’s house. He used the drive to calm himself down, because the closer he got, the more his nerves started to act up. Uselessly, he kept reminding himself that this _wasn’t_ his first date (but it was with _them)_ , that he knew what he was doing (he _really fuckin’_ didn’t), that whatever they planned would be fun (would it?).

Even with all that going on in his head, hell, probably because of it, he was relieved when he pulled up and parked in one of the guest spaces off to the side of their house. With a fond pat to Baby’s steering wheel, Dean hopped out and pocketed his keys.

One deep breath in to calm lingering nerves and Dean walked up to the door. Knocked firmly and stood back a little to wait. After a couple seconds the door swung open, and there stood Jimmy. Wearing a turquoise hoodie with ‘STFU’ written across the front like college lettering, a pair of dark jeans, looser than anything Dean had seen him in, and a pair of fuzzy purple slipper boots that Dean couldn’t help but smirk at, Jimmy squinted at him and scrubbed a hand through his spectacularly messy hair.

“Mmm.” Jimmy hummed sleepily at him.

“Mornin’ Sunshine.” Dean returned with a grin.

Jimmy’s eyes narrowed even more and there was no mistaking his displeasure at Dean being so cheerful that early in the morning. Despite that, Jimmy shuffled forward out the door and slumped against Dean, like he couldn’t handle keeping himself vertical anymore. Dean’s arms wrapped around him just in time to keep him from sliding down his body onto the ground.

“Don’t be so dramatic, Jimmy.” Castiel chided a second later when he slipped out the door and shut it firmly behind himself.

Unlike Jimmy, Castiel was perfectly put together with a neat grey wool pea coat along with a deep blue scarf and black jeans that fit him nicely. His hair looked like it’d at least seen a brush today, even if it wasn’t particularly neat.

Dean figured he fell somewhere in between, which made them look really odd together, and didn’t help at all with Dean’s attempts to guess where they were going.

With an exasperated roll of his eyes, Castiel leaned over Jimmy and pressed a quick, soft, good morning kiss to Dean’s cheek before he started to walk down the front steps to the black stretch limo that was parked idling out front, “You’ll need to let him go so that we can actually _leave_ Jimmy. You can sleep in the car.”

Jimmy mumbled something vaguely intelligible that sounded like an extremely petulant ‘You can go fuck yourself in the car’.

Sometimes it was so obvious that Jimmy and Castiel were brothers, appearances aside, that Dean would almost forget there was more.

Jimmy did straighten up though, enough to give Dean a little uncharacteristically shy smile before he pushed up on his toes to kiss him. Dean blinked, a little stunned. Wasn’t the first time he and Jimmy had kissed, but he’d never seen Jimmy get nervous like that. There was something just really freakin’ cute about the way Jimmy’s cheeks pinked up too.

Right after, Jimmy laid his head back down on Dean’s shoulder to hide his face which just made it even cuter. Dean let Jimmy rest there for a moment while his brow furrowed and his mouth formed a small frown. Jimmy was brash and unapologetic on a good day. Seeing him like this reminded Dean how vulnerable Jimmy really was, how easily Dean could fuck him up.

Reluctantly, Dean cleared his throat, smiled softly at Jimmy before he squeezed his shoulder and turned him in the direction of the limo, which was right about when he noticed that Castiel was _climbing into a limo_. Dean’s mouth dropped open a little before he spoke, “Seriously? We’re taking a limo? Doesn’t that seem a little, I dunno, excessive to you guys?”

Jimmy looked back over his shoulder with a raised brow at Dean before he succinctly replied, “Nope.”

Then he reached down and grabbed onto Dean’s sleeve, dragged him over and into the limo. Castiel was already seated in one of the back seats and with a yawn, Jimmy stretched out along the side seat on his back, arms pillowed under his head. Dean smiled warmly at Castiel, “Looks like I’m sitting with you.”

Castiel’s smile back was just a little forced, and Dean wondered what that was about. Quiet classical music was the only thing that kept the ride from being completely silent, but not from being uncomfortable. Dean shifted in his seat, and replayed the morning so far in his head, tried to figure out what he’d done, because Castiel had seemed totally normal before he walked to the car. Every once in awhile, Castiel glanced over at him, and Dean felt even shittier, because it must’ve been something big, but he couldn’t figure it out.

Oblivious to the tension, Jimmy fell asleep not long into the drive, his breathing evened out and once it’d been deep for a good while, Castiel finally turned in his seat to look more fully at Dean. Mouth set in a small frown, he pulled his inside leg up to rest against the cushion with his ankle tucked under his other knee.

“I’m not going to let him get hurt, Dean.” Castiel said quietly, seriously and Dean was totally at a loss because, _what?_

“Huh?”

“If this… if _he_ doesn’t work for you, then we should just put an end to this now.” Castiel replied in a low, hurt voice, which just confused Dean even more because really, what the actual fuck?

“Cas, what’re you-”

“I saw you,” Castiel said, eyes intent on Dean’s like he was studying his reaction. “After Jimmy kissed you. You didn’t exactly look happy to have been kissed.”

And oh, _that._ A smile spread Dean’s lips and Castiel tilted his head curiously, he probably hadn’t expected Dean to grin right then, “No.. Cas, I just- I realized Jimmy talks a big game but he really… I don’t wanna hurt him either. I like him too.”

Relief flashed across Castiel’s face and his entire body relaxed, “I’m glad. Just don’t be afraid to _show_ that you like him. I know Jimmy comes across as extremely confident, but he has his insecurities too.”

Warmth flooded Dean’s chest for Jimmy, couldn’t imagine him worrying whether or not Dean liked him. He’d need to work on being more expressive because Jimmy and Castiel both deserved that much.

“I’ll try harder.” Dean promised.

The rest of the long drive passed with quiet conversation, much lighter topics until Jimmy finally woke shortly before they arrived. Dean knew they were getting close to their destination because Jimmy practically vibrated excitement, flitting from one topic to the next in what Dean could only assume was an attempt to distract him from looking out the windows.

Right before they took a sharp right, Jimmy squished himself between Dean and Castiel, wrapped his arm around Dean to cover his eyes and told him not to peek. Dean smirked but he went with it. A minute or so later, they rolled to a slow stop and Jimmy made Dean promise to keep his eyes closed. Tugged him out of the car with Castiel right behind them.

“Okay!” Jimmy exclaimed once they were all standing outside the limo. “You can look.”

Dean’s eyes blinked open and his brows shot up a bit at the huge ski lodge in front of him; Gorgeous with dark-stained logs, and stone facing, big pointed roofs, and a ton of windows, it looked like something out of a travel magazine. Rustic, but modern and covered in a fine layer of snow that sparkled in the sun.

Nice, skiing was something Dean had done once, a few years ago on a school trip. He’d been okay at it, even if he couldn’t really remember the details on how, exactly. But he’d liked it, so score one on that front.

“So?” Jimmy prompted excitedly, “What do you think?”

“Gotta say, I’m impressed. I definitely didn’t think skiing when you said activity.” Dean said with a smile.

“Have you ever skied before?” Castiel asked.

“Sure, once. Long time ago though.” Dean admitted. “But I don’t have any gear with me.”

“Duh,” Jimmy said. “Would’ve ruined the surprise if we asked you to bring some. We brought everything you’ll need.”

Huh, okay then, good thing they had extra snow gear, Dean thought, hopefully the twins were closer in actual size to him than they looked.

“We got lessons too, because we weren’t sure if you’d been skiing before.” Castiel said. “The instructor’s supposed to be the best one here.”

“Aw, you guys probably could’ve just taught me.” Dean protested, it probably would’ve been fun to learn with them.

Castiel shrugged a shoulder, “Neither of us has taught anyone to ski before, seemed more prudent to have a professional do the honors.”

“Yeah, okay.” Dean agreed, “Makes sense.”

“Let’s go check it out.” Jimmy said enthusiastically, “We’ve never been to this one before, but it looked nice online.”

Dean couldn’t help but grin, and just as Jimmy took a step toward the lodge, Dean reached out and laced their fingers together. Jimmy smiled brightly at him, and Dean’s heart gave a little squeeze in his chest. A quick glance behind him showed Castiel had his own warm smile aimed at the two of them.

“Go ahead,” Castiel encouraged, “I’ll help the driver with our bags.”

“You sure?” Dean asked, “I could help.”

“No, go on. You and Jimmy can let them know we’ve arrived.”

“Dean, come _on_!” Jimmy said, emphasized it with a tug to Dean’s hand.

Hard to say no to that face, so Dean just shared a look with Castiel before he let Jimmy drag him into the lodge. Inside was every bit as fancy-rustic as the outside was. With wide walnut hardwood flooring, and an elegant dark wood front desk, the lobby was brightly lit with natural light complemented by chandeliers that looked like tiny warm lamps all clustered together.

The interior walls were cream colored drywall accented with big wooden beams that matched the flooring. A cute, peppy blonde girl was waiting inside the entrance with a clipboard.

“Mister Novak?” She questioned as she looked back and forth between the two of them.

Jimmy raised his hand silently.

“Great, if you’ll just follow me we’ll get you guys all settled.” She said with a grin before she spun around.

Dean couldn’t help but watch for a minute as the girl walked away. Her snug little pencil skirt had the dual benefit of showing off her legs and making her ass look _really_ nice as it shifted beneath the fabric.

“You know-”

Dean jumped a bit when a voice sounded from the side of him that’d previously been vacant.

“It’s really rude to look at other people while on a date.” Castiel said dryly.

Dean’s cheeks heated with a guilty flush. He was about to apologize when Castiel spoke again.

"Really Jimmy, I think you've already got more than you can handle with us, don’t you?”

Eyebrow raised, Dean turned his head to look at Jimmy who was sporting a very guilty expression and not looking at anyone. Interesting. Guess that answered _that_ question about Jimmy.

Then Castiel started forward to catch up with the woman so Dean took advantage of the moment to lean over and whisper to Jimmy.

“Hey man, it’s cool. That skirt looks pretty good on her.”

Jimmy brightened up quickly before his expression changed again, slipped into something a little more… lascivious.

“It does, but it’d look better on me.” Jimmy said with a wink before he moved to follow Castiel.

Dean had to hang back for a moment as he adjusted himself. 

A few minutes later they’d been led into a big rental equipment room, their bags safely stowed in a locker, and their snow gear spread out over a couple of plush chocolate brown leather benches. They’d just finished giving their boot size to the guy working the room, when Dean noticed how empty the place was. Usual crowd must be early birds, because it was deserted and they were the only ones in the place.

When Dean looked back at them, Castiel had already pulled on a pair of white ski pants with black knee patches and was shrugging into a bright orange winter coat, while Jimmy was pulling up his own neon yellow ski pants. Not wanting to fall behind, Dean quickly kicked off his boots and stepped into the, thankfully, plain black ski pants they’d brought for him. Must’ve been Castiel’s because Dean got the feeling Jimmy didn’t do subdued winter wear.

Jimmy had just gotten into his bright sky blue coat with neon yellow accents, which looked, really fuckin’ good on him, Dean had to admit, when Dean pulled on his red coat and noticed how well it fit him. Which was weird. Because Jimmy and Castiel were both a bit smaller than him and if this was an old suit, shouldn’t it be a little snugger than it was?

“What’s wrong?” Castiel asked, of course he’d noticed Dean’s little moment there.

“Nothing, just noticed this fits really well. Thought it’d be tight, ‘cause it’s yours, right?” Dean replied, and then put two and two together. “You bought it for me, didn’t you?”

“Of course.” Castiel replied easily, “Like you said, ours would be too small.”

“But…” Dean trailed off, gathered his thoughts and tried again, “But, you didn’t even ask if I already had snow gear.”

He did, in fact, own snow pants and a winter jacket. Sure, yeah, alright, they’d been bought before his last growth spurt so they were kinda short on him, but point was, he had ‘em.

“Surprise, remember?” Jimmy said with a smile, like he didn’t really get Dean’s concern, and why would they, they’d probably never even considered the expense. Dean’d seen the outside of their house, the limo, a snow suit had probably seemed like a tiny thing to them, but Dean shifted uneasily at the reminder they were spending money on him.

Jimmy’s smile faded just a bit, and Dean realized he hadn’t answered. Castiel’s earlier warning swam to the forefront of his mind, and he pushed down the uncomfortable feeling that’d started to grow in his stomach, because damnit, Dean was gonna make sure Jimmy and Castiel had a good time today, and if that meant ignoring his own pride, then he’d do it.

“Yeah, sure. Just caught me off-guard is all.” Dean replied, then a thought occurred to him, “How’d you guys know my size?”

Castiel grinned at him, “Well, we do spend a truly extraordinary amount of time watching you. It came in handy when we needed to guess.”

“Yeah,” Jimmy agreed, “Not our fault you’re easy on the eyes.”

Dean’s cheeks flushed pink, and just as he opened his mouth to reply the dude that’d taken their shoe sizes came back with three pairs of ski boots for them.

He’d barely set them down and walked away before Dean was up out of his seat and on his knees in front of Jimmy. Unnecessarily, really, because Jimmy was perfectly capable of putting on his own ski boots, but that didn’t stop Dean from helping him into them and fastening the buckles.

After he finished buckling up his boots, Dean looked up into Jimmy’s bright blue eyes with a little smirk on his face and let his hands slide slowly up Jimmy’s calves. Watched while Jimmy’s eyes glazed over, so fucking hot. He’d just started to press them firmly up the front of Jimmy’s thighs when Castiel cleared his throat. Startled both Jimmy and Dean into looking over at him… and the guy next to him.

Slim, a little shorter than Castiel, but powerful looking in his black snowsuit embroidered with the ski lodge’s name, goggles perched on top of his head, and black gloves in his hand. Five o’clock shadow, pale green eyes too, guy was pretty good looking. Not that Dean was, you know, looking.

The guy’s eyes flicked to Dean’s hands, still on Jimmy’s thighs, and Dean pulled them away, slightly flushed and kind of embarrassed. They were in public after all.

“Jimmy, Dean, meet Mick Davies. He’ll be our ski instructor for the day.” Castiel said.

“Hey.” Dean said as he stood up and got into his own boots, Jimmy just smiled and waved.

“Mornin’ lads.” Mick said in a rough British accent that Dean instantly kinda disliked. “When you’re all ready to go, we’ll hit the bunny hill and run through the basics. Like as not, it’ll take us roughly an hour or so. At which point, we’ll break for lunch and then head over to one of the harder trails via snowmobile. We’ll catch the lift up and run through it a few times. By then, you’re likely to be pretty worn out, and we’ll call it a day. A pretty reliable source tells me you’ve got appointments at the spa late this afternoon, so we’ll make sure you’re back on time.”

“Perfect.” Castiel said.

“Great.” Dean mumbled at the same time Jimmy cheerfully said, “Sounds good.”

Fast as he could, Dean worked to secure his boots, and by the time he’d finished, a pair of skis and poles for each of them had been dropped off. Dean tugged his gloves on and grabbed his gear, but before he could follow Castiel and Mick outside, Jimmy stopped him.

“You’re forgetting this.” Jimmy informed him as he tossed Dean a helmet.

A neon pink helmet. Dean blinked down at it uncomprehendingly for a moment, brows raised. Jimmy couldn’t be serious, he wanted Dean to wear a _pink_ helmet? Really?

The strained silence broke with Jimmy’s loud laugh, “Holy shit, your face, Dean. I’m just kidding, that’s mine. Here.” Jimmy held out a black helmet with red detailing and a built in visor, then smirked broadly at Dean. “Probably shouldn’t be so threatened by a color though.”     

“Probably shouldn’t.” Dean agreed, Jimmy wasn’t wrong, but Dean was still glad for the much more muted helmet.

They swapped helmets, grabbed their gear and headed out in search of Castiel and Mick. When they all got to the bunny hill, Mick ran through a few basic instructions, like how to slow your descent with exaggerated S’s and turning your feet in to form a wedge to slow down or gradually stop. He reminded them that forcing yourself to fall was always preferable to crashing into something. Castiel and Jimmy stayed there and listened to all of it, went along with it while Dean learned.

Which Dean thought was really sweet of them, until on his fourth run down the bunny hill, thanks to some unfounded confidence, he wiped out. Super fucking embarrassing, and didn’t help that Jimmy doubled over laughing when he expertly skied to a stop next to him. So Dean did what any nearly full-grown male would do; He stealthily scooped up a handful of snow and pegged Jimmy in the face with it.

Jimmy spluttered and Dean laughed from his position on his back in the snow. Castiel’s laugh rang out from a few feet away and Jimmy glared at him before he bent and scooped up his own snowball then pelted it hard at Castiel. Jimmy’s aim would’ve been great if Castiel hadn’t already started to dive out of the way. Which meant Jimmy missed by a hair and then ended up with another faceful of snow when Castiel threw a snowball right back at him.

And that just wasn’t fair, so Dean took pity on Jimmy, and managed to hit Castiel in the chest with a loosely packed snowball. Castiel shot him a betrayed look and Dean laughed again, both hands held up, “Truce?”

Briefly, Castiel’s eyes narrowed before he finally agreed, “Only because you clearly need more time with Mick before we break for lunch.”

Dean rolled his eyes and he almost missed it as Jimmy helped him to his feet, but he heard Mick say in a fairly flirty tone, “Now don’t project, Castiel. Are you sure I can’t teach you a few new things?”

“Thank you, no, I’ve had private lessons.” Castiel answered oblivious to the undercurrent in Mick’s voice.

Dean would’ve laughed if he wasn’t internally fuming over the damn comment Mick had made. Stupid to be pissy over it when it’d gone right over Castiel’s head, and even though he wanted to say something, he didn’t wanna come off like a jealous boyfriend, which he wasn’t. A boyfriend. This… this was just a date. If Jimmy didn’t feel the need to, why should he? Still, Dean wasn’t gonna be leaving the two of them alone anytime soon.

The rest of the hour before lunch passed unexceptionally. Dean was a pretty quick learner aside from his little fall earlier. By the time they called it quits, he’d already gotten the hang of it for the most part, even if he was still cautiously taking it a little slow.

After they got to the bottom of the bunny hill, Mick led them over to a rack where they left their skis. Dean vaguely noticed the absence of other skis, but didn’t think anything of it because he was too busy watching how closely Mick was walking next to Castiel. Relieved as fuck, was how Dean felt when they got through the doors and Mick told them he’d be back to meet them in an hour to head further up the mountain by snowmobile to the lift for one of the harder trails.

For a second there, he’d worried Mick was about to invite himself to spend lunch with them, and no, dude, wasn’t gonna happen. Thankfully it hadn’t come up and Mick walked off back through a staff only door while they headed to peel themselves out of their jackets, snow pants and ski boots before they pulled their own shoes back on.

Once they’d all gotten into them, they made their way into a cozy dining area with a large stone fireplace, a couple of couches around it and a coffee table directly in front of it. There were tables with red leather chairs too, but Jimmy grabbed hold of Castiel’s hand excitedly and dragged him over to one of the couches. Dean followed behind them with a smile on his face, and thought to himself, how fucking different this felt from that day he’d watched them together for the first time.

Instead of feeling jealous when Jimmy curled up in the corner and pulled Castiel down close enough that they were basically cuddled up, Dean just had this warmth that suffused his chest and made him smile like a giant dork as he walked over.

“Dean,” Castiel spoke right before he was about to drop down onto the adjacent couch, “I…” Castiel’s cheeks, already pink from the cold, darkened just a little more with a pretty flush of color, “There’s plenty of room over here… with us.”

Holy, fucking, cute. Yeah, like Dean could ever say no to that, “Oh, yeah, okay.”

Which was how the three of them ended up crammed together on a couch while food was brought out. Castiel and Jimmy must’ve ordered ahead, because it hadn’t taken long at all, and nobody had even brought a menu over.

Lunch was delicious and after the plates had been taken away, the server appeared with three mugs of hot chocolate topped with a small mountain of whip cream. Dean’d just taken a cautious sip of his when he looked over and noticed Jimmy, upper lip covered in cream.

Right about at the same time, Castiel noticed too, and he scoffed a little, smile warm before he leaned in and licked it off Jimmy’s lip, finished it up with a lingering kiss that left them both a little flushed and breathless with broad smiles and warm eyes.

For a second, Dean was slightly surprised because they were in public and Jimmy and Castiel were usually so careful outside of school, but the room was basically empty anyway and what staff was actually there hadn’t seemed to notice or care.

So when Jimmy flashed Dean a little smirk before he reached a hand up into Castiel’s hair and tugged him back in for another kiss, Dean just felt happy that they had the chance to be together so openly. Leaned back in his seat and casually enjoyed the show until Jimmy tried to dip his hand under the back of Castiel’s waistband and Castiel sighed an exasperated _Jimmy_ into his mouth before he pulled back.

Jimmy just grinned while he took another big sip of hot chocolate with a quick glance over at Dean like he was trying to gauge his reaction. Which was very fucking favorable, thank you very much, so Dean smirked back at him before he shifted in his seat a little and drank a slow sip.

Before long they were suited up again and met Mick back out at the doors. Dean wasn’t exactly impressed when they’d gotten outside and Castiel had ended up on the back of a snowmobile with Mick. He’d fought down a little surge of irrational jealousy, and tried to concentrate instead on how hot Jimmy was all focused on driving their snowmobile.

A hard afternoon of skiing followed, and luckily for Dean there were no more spills. He was pretty proud of himself, actually. A little sore in muscles he didn’t even know he had, but still, proud. The only bit of a damper on his mood were a couple other little things Mick had said. Nothing as obvious as the comment before lunch, but enough to prickle under Dean’s skin. Neither Castiel or Jimmy seemed bothered by it, or really to have noticed, though.

When they’d gotten out of their skis and stowed them for the snowmobile ride back, Dean had suggested that Castiel ride with him instead, since he’d ridden with Jimmy on the way up, but Castiel had just brushed it off, said it was good for him and Jimmy to spend time together. He couldn’t really argue with that without looking like he was being a dick about Jimmy even though that wasn’t the case at all. So Dean had smiled at them and agreed, hoped it didn’t sound or look forced.

He climbed onto the snowmobile behind Jimmy again, went to grab the handholds, but Jimmy sent him a coy smile over his shoulder and reached back to pull Dean’s arms around his waist. Dean chuckled, but shifted so that he was pressed up against Jimmy’s back and felt the rumble of it through his chest when Jimmy hummed his approval.

Then he took off, and they were following Mick back the way they came. Heated seats kept the ride a little more comfortable, but the cold wind rushing over them as they sped through the snow was kind of a thrill. Involuntarily, Dean’s arms tightened around Jimmy as they took a tight corner, definitely _not_ the way they came, what the hell?

Judging by the way Jimmy tensed up, he was wondering the same damn thing about the detour Mick had taken. It was hard to enjoy the gorgeous scenery when Dean was too busy mentally ripping Mick a new one.

About fifteen minutes later they got back to the ski lodge and Dean climbed off the snowmobile, ready to tear into Mick, but one look at Castiel’s flushed, exuberant face when he pulled off his helmet, instantly cut his anger short.

Eyes bright with excitement and adrenaline, Castiel was fucking hot and Dean couldn’t help but stare. His brain kicked back into gear when Jimmy threw an arm over his shoulder and leaned in to whisper in his ear, “Looks extra hot when he gets excited, doesn’t he?”

“Damn right, he does.” Dean agreed easily.

Mick tagged along with them to the spa’s changing area, engaged in a quiet conversation with Castiel. Dean was irritated, but Jimmy pulled him along and excitedly talked about the massage they were about to get after they showered.

“So, I was thinking, we really should do our part to conserve water.” Jimmy said with a wide slightly wicked grin, and Dean raised one eyebrow.

“Yeah, ya think so?”

“Mhmm, one shower would waste much less water than three.” Jimmy replied.

A half a second later, Dean knew something was off because the _Jimmy_ that should’ve followed that come-on never came. Jimmy looked at Dean just as concerned and they turned around at the same time. Castiel and Mick were still at the other end of the hall and Mick stood way too close to him.

Castiel still had a small smile on his face, but almost simultaneously, Dean and Jimmy started to walk back, just in earshot when Mick said, “So, was the ride too much? You enjoyed the trip there so, I thought I’d give you a bit more of a taste. I know it wasn’t planned.”

“No, it was great.” Castiel said, cheeks still pink and eyes still bright.

“Good.” Mick’s hand ran slowly up Castiel’s arm, “I reckon you could handle _any_ ride without breakin’ a sweat.”

Castiel’s eyes widened and his lips parted like his brain finally caught up to what was happening as Mick dragged his hand back down his arm, “Mick, I-”

Castiel didn’t get the chance to finish his thought, because Dean finally gave in to the possessiveness that’d roiled in his gut all day; Grabbed Mick’s shoulder tightly and growled, “I'm gonna need you to take your hand off what's ours.”

Mick’s eyebrows shot up while he did as he was told and took a step back, confusion all over his face, “Aren’t you and-” he nodded at Jimmy, who stood just as menacing right next to Dean.

“He _said,_ he's ours.” Jimmy said, voice low and dangerous and fuck if it didn’t send a little whisper of arousal down Dean’s spine.

Mick nodded, eyes big, but free of malice, “Right, well in that case, my apologies gents. If I’d known…” Mick nodded again like he was confirming just how fine all of this was. “I’ll just leave you to it, then.”

As Mick quickly retreated, Castiel glanced over at Jimmy and Dean, a look on his face like he wasn’t sure if he should be amused or offended or turned on, or maybe all three at once, “I’m yours?”

“Duh.” Jimmy said then checked Dean out before he turned back to Castiel, “He’s fucking hot when he’s jealous.”

Dean rolled his eyes, “You were jealous too, Jimmy.”

Jimmy shrugged noncommittally, “So, where are we on the one shower thing? ‘Cause I don’t know about you guys, but after that, I definitely think we should share.” 

Castiel’s eyes were dark with want for a few seconds before he managed to school his face to something more neutral, “Separate showers.”

“Fine.” Jimmy replied way too easily. “Don’t say I didn’t give you fair warning though.”

“What’s that supposed to mean?” Castiel asked, probably just as confused as Dean was.

In reply, Jimmy smiled innocently at them before he walked into the changeroom. Whatever he meant, he didn’t explain himself, and they all took quick, separate, showers before they pulled on the fluffy white robes the lodge provided for the spa.

They walked down a wide staircase with a gorgeous wrought iron railing that featured a leaf design, past a ridiculously beautiful pool with turquoise water and a marble bottom, surrounded by thin hardwood planks that reminded Dean of saunas, and through a pair of white double doors into the spa’s waiting area.

Inside two very tall, very good-looking men and a pretty petite brunette woman in scrubs were waiting. The brunette quirked a lopsided smile at them.

“Well, hello boys. So, which one of you gets me?” She asked with a grin just this side of inappropriate.

“Cas!” Jimmy and Dean instantly exclaimed, and Castiel smirked at them while the brunette raised her eyebrow in question.

“I think your lack of male genitalia makes them feel less threatened by you.” Castiel explained.

“Ah, gotcha.” She said, “But I dunno guys, these hands are pretty magical.”

“We’ll take our chances.” Dean said while Jimmy nodded his agreement.

“Suit yourself.” She replied before she led them into a room with three massage tables lined up side-by side with enough room in between for a person to comfortably walk.

After she’d shown them in she left them with instructions to remove their robes and get comfortable face down under the crisp white sheets. Politely, Dean kept his eyes to himself and stripped off his robe before he crawled onto the table then draped the sheet over himself. Don’t get him wrong, fuckin’ right he wanted to look, but it seemed rude. So he went with his gut on that one.

Once they were all settled a tense sort of silence pervaded the air. Dean couldn’t help thinking about the fact that all three of them were naked barely feet from each other. He didn’t need to see Jimmy and Castiel to picture them beneath the sheets. He wondered if they were thinking about him too.

“Dean?” Jimmy stage-whispered.

“Yeah?”

“Bet you wish we’d shared that shower now, huh?”

You can’t hear eyes rolling, but Dean would swear he heard Castiel’s roll right then. Luckily Dean was saved from answering, which for the record, woulda been an enthusiastic fuck yes, by a light knock that came on the door before it opened a crack.

“All set guys?”

“Yes.” Castiel answered for them with a tiny hint of exasperation in his voice, probably only noticeable if you spent an obscene amount of time analyzing his voice. Which Dean did.

A few minutes later, Dean was just getting used to the firm, warm hands that were gliding over his back and shoulders, slick with massage oil as they dug into tense muscles, when it started. Almost barely audible at first, Jimmy let out little breathy groans and moans every once in awhile. Dean assumed whenever the masseur found a particularly tense spot, but pretty soon Jimmy’s little noises grew louder, and Dean felt himself harden against the table.

He bit his lip and tried to keep from squirming, but fuck, the sounds Jimmy was making were so damn _hot._ And there were hands on him, and sure, it wasn’t supposed to be sexual, but it’s not like Dean’s _body_ knew that. Especially with Jimmy’s goddamn moans echoing loud in his ears.

And then suddenly there was a flurry of movement and feminine laughter to his right and Dean looked up just in time to watch Castiel with his sheet wrapped around his waist as he grabbed a clean washcloth off the counter and shoved it into Jimmy’s mouth, “I thought you might like some help keeping quiet, Jimmy.”

If Dean hadn’t been hard before, he definitely would’ve been now, between Castiel’s voice and the fact he’d basically just gagged Jimmy. He had to take some deep breaths to calm himself down, and as Castiel walked back to his table he glanced at Dean. Smirked like he knew exactly the effect that’d just had on him and Dean had to catch his breath all over again.

Eventually though, with Jimmy effectively silenced, he relaxed into the massage, and as the tension in his body was slowly worked out, he drifted in a half-awake state until it was over. Boneless and warm, he slowly came back to himself when the masseur told him to take his time and get up when he was ready, Dean hummed his agreement.

Yawning, he opened his eyes and Castiel was standing beside him, already in his robe, Dean’s in his hands. So Dean sat up and pulled it on, fastened it before he carefully stood up, “Thanks.”

“Of course. Jimmy, you can take the washcloth out of your mouth now… If you’re ready to behave.” Castiel said.

Jimmy glared but complied, and tossed the cloth into the hamper in the corner of the room before he got his robe on too.  

They walked back the way they came, Dean closest to the wall and Jimmy between him and Castiel. As they were passing the pool Dean caught Jimmy’s grin a half a second before he shoved Castiel in. Jimmy burst out laughing as Castiel surfaced, eyes narrowed at him.

Dean’s surprise was short-lived and he chuckled as he scooped Jimmy up bridal style and jumped in the pool too. Indignantly, Jimmy splashed Dean when they came up for air. Which was basically how they all ended up laughing, engaged in a water fight until Dean noticed Jimmy’s robe had floated up around his waist, that _all_ of their robes were floating up.

Lightening fast, Dean’s hand shot down to pull his robe down, cheeks faintly pink with laughter that embarrassment only darkened. Even if it was kind of ridiculous to be embarrassed, because two of three people in the pool had seen his dick before and the other one had tasted his come and that was just-

Not an appropriate thing to think about if he didn’t wanna compound his embarrassment by adding in a boner. Almost instantly, Castiel noticed the change in Dean’s demeanor and pushed his own robe down too. Wasn’t like you could really see beneath the rippled water, but still.

“We should go get showered off, I’m famished.” Castiel said, and thank God, because Dean was starving too. _“Separate showers, Jimmy.”_

“I wasn’t gonna-”

“Yes, _you_ were.”

“All I’m saying is, it’s a _great_ idea, Cassie.”

Dean just grinned happily at the two of them until they both looked at him, Castiel with a little frown and Jimmy with raised expectant eyebrows.

“What?” Jimmy finally asked.

“Just thinking how adorable it is when you two do that.” Dean said as innocently as he could manage.

“Is not.” They both said at once, and then Castiel rolled his eyes, but his lips turned up in a little smile.

Jimmy’s stomach chose right then to formally petition their attention with a loud growl and they took it as their cue to get out. Sopping wet, Castiel mumbled about how _this is why you don’t push people into pools, Jimmy,_ they made their way back to the change room and quickly showered before they dressed in clean clothes.

Dean’s black jeans fit perfectly though the accompanying black sweater with a wide royal blue stripe across the chest and arms was a tad snug. Guess there were some things the twins couldn’t accurately guess. Or, more likely judging by the way they both eyed him once he was dressed, it’d been a conscious decision.

A table had been set up in front of the fireplace they’d lounged in front of during lunch. Firelight made the expensive settings glow warmly. The food was hot and waiting for them, a fact that Dean’s stomach was seriously grateful for. Delicious Kobe beef burgers with some sort of fancy truffle butter… or something? Dean didn’t really catch what it was, too busy staring at the look of unadulterated desire on Jimmy’s face while he eyed the burgers. Was _still_ staring at him when he took his first bite, and honestly, Dean’d never been jealous of a burger before, but _holy fuck._

The corners of Castiel’s mouth twitched up a little while he watched Dean, “In case you can’t tell burgers make Jimmy very happy. I let him pick out what we were having for dinner and dessert. I expect dessert will be lemon meringue pie.”

“Ha.” Jimmy said around a bite of burger, “Shows what _you_ know. I picked something different just for you two.”

“Aw.” Dean said, only a little disappointed, “I’d a been cool with pie… If, uh, ya know, it’s your favorite.”

“You’ll like this better.” Jimmy assured him. “Trust me. And seriously, try the burger, it’s fucking fantastic.”

Jimmy was right, it was fantastic. Didn’t take all that long for the three of them to demolish them and their fries. Which were also fucking amazing, Dean had to admit. Either he was really damn hungry (he was, but still) or this food was just ridiculously good, though he still wasn’t entirely sure what the hell a truffle was. He _thought_ it was some weird chocolate thing but evidently not.

They finished their supper, washed down with sparkling juice because Jimmy said Castiel wouldn’t let them have wine. Something about not getting their date drunk, which Dean laughed at, because he’d had much harder drinks than wine and been fine. But whatever, he didn’t need a drink to enjoy spending time with Jimmy and Castiel anyway.

Once their plates had been taken away, the server returned with a large silver platter full of strawberries stuffed with some sort of white filling. At Dean’s curious look, Jimmy filled in the blank, “Cheesecake stuffed strawberries.” 

Shortly after the server left, Dean found out exactly why Jimmy was so sure he’d like it better than pie; after he picked up the tray and moved the three of them back over to the couch they’d occupied earlier Jimmy plucked a strawberry from the tray and climbed onto Castiel’s lap, hand-fed him bites until it was gone and then leaned in slow to kiss him. Dean sat back and watched as Jimmy licked and sucked every last taste of the dessert he’d fed Castiel from his mouth. Hot as fucking hell, and Dean didn’t look away for a second.

And even then Dean was caught off guard when Jimmy pulled away from Castiel with a final suck of his bottom lip, grabbed another strawberry and crawled over to straddle _his_ lap. Jimmy brought the berry to his lips and warmth rushed through Dean along with the sweet-tart taste of it as he bit into the strawberry.

That kind of attention, care, wasn’t something Dean was used to and for some reason it felt _way_ more intimate than anything Dean’d done before. So maybe he was a little surprised and hesitant that first bite, but by the time it was gone and it was _his_ mouth Jimmy was licking his way into, Dean all but melted into it.

Into Jimmy’s tongue as it brushed over his and flicked at his soft palate, teased along the inside of his cheeks, and he hardly noticed when Jimmy started to rock down onto him, but Castiel cleared his throat and Jimmy smirked against his lips before he pulled away.

With a wry smile at Castiel, Dean picked up a strawberry and returned the favor, hand-fed it to Jimmy who of course took the opportunity to lick and suck every bit of juice from Dean’s fingers before Dean got to watch while Castiel kissed him deeply, inches away. Warmth and arousal a slow burn in his gut while he did.

After that they fed themselves, and talked about their day, about their plans for tomorrow and anything that came to mind and before long they were nearly ready to leave. Castiel had already asked for their bags to be returned to the limo, and just as Dean stood up to stretch the concierge walked in and handed Castiel the bill. Which Dean couldn’t help but peek at out of curiosity. What did a date like this go for anyway?

"Jesus Christ we didn't eat _that_ much!" Dean said wide-eyed as he caught a glimpse of the total just before Castiel handed it and a credit card back to the concierge. And since when did the _concierge_ work the dining room?

"Oh no, that would be an extravagant amount for food even for us." Castiel said as he stood from his seat. "That was the bill for the day."

"Still Cas, that was… _a lot_ of zeros for some ski lessons, food, and massages."

Jimmy shook his head and smiled at Dean like he was the silliest person on the planet, "That was to rent the resort for the day."

"Come again?"

"Didn't you notice we were like, the _only_ ones here?" Jimmy asked, head tilted just a little and eerily reminiscent of Castiel for a moment.

"Just figured it was slow… kinda outta the way." Dean said like he was only just realizing how dumb that assumption sounded, because a place like _this,_ yeah, no way it’d be empty on a Saturday.

"We wanted to ensure that we would be uninterrupted during our date and..." Castiel paused to glance at Jimmy, "uninhibited without prying eyes and judgement."

Dean’s head spun at the implication. Of course they’d want that. Dean didn't begrudge them that _at all_ . But how could _he_ give them what they needed if _that's_ what they needed. He didn’t have time to dwell on his thoughts though, because rather quickly he found himself with a hot guy under each arm and four arms wrapped around him, which sure as fuck made walking awkward but Dean wasn't even remotely gonna complain.

They ended up in the backseat with Dean in the middle, Jimmy and Castiel tucked up against him, heads on his shoulders while they drove. It didn’t take long at all for their extremely busy day to catch up with all of them. One by one they drifted off to sleep.

The first thing Dean became aware of when he woke was that the car had stopped moving. The second thing he noticed was actually two things; Castiel and Jimmy’s warm, comfortable, weights draped over him. Careful not to jostle them he peeked down at them in the dim lighting of the limo, and let out a slow exhale as he did.

God, they were so damn gorgeous, both of ‘em, so fuckin’ perfect and way, way, way too fuckin’ good for him. So far out of his league it wasn’t even funny. Too smart, and awesome, not to mention the fact he’d never be able to give them even a little bit of what they’d done for him back. How was he supposed to be good enough for them when he didn’t have a fucking clue how to?

All he knew while he stared down at their flushed, sleepy faces was that he wished he was. Like his thoughts had intruded on their happy little bubble Castiel yawned and stretched, which jostled Jimmy into wakefulness too.

One minute they were blinking awake and the next they were trading slow, sleepy kisses with Dean. Lazy-soft brushes of tongues and lips that blended into one another, heated in a muted sort of way. Hot and easy and so good, Dean just laid back and let them take charge of it. Loved the way it got messier the longer it went on until they were kissing him at practically the same time.

Pleasure rolled through him in slow swells, but without any rush. Just a mixture of indulgence and satisfaction that seeped into everything and Dean forgot what the hell he was supposed to be caring about, because there was nothing more important right then, than _this._ Than being _with_ Castiel and Jimmy and making them feel as good as they were making him feel.

And then Jimmy’s hand slowly slid from where he’d been cupping Dean’s neck down his chest, thumbed over his nipple on the way and drew a little gasp from Dean. Just as his fingers started to slip the buckle of Dean’s belt open and his palm brushed over Dean’s cock, Castiel’s shot out to still him, “That’s enough, Jimmy.”

Dean stifled a groan and focused his attention on _not_ rolling his hips up into the warmth of Jimmy’s hand because fuck, it was right goddamn _there._

“But he’s so _hard,_ Cassie.” Jimmy whined while he looked at Castiel with a set of puppy eyes that Dean would probably do anything for if they were directed his way. Castiel though; he just stared back until Jimmy finally pouted and moved his hand away.

“Time to get you home, Dean.” Castiel said softly, and Dean already missed the warmth of them, but Castiel was right so Dean nodded and followed him out of the limo, Jimmy behind them.

The two of them walked him to his car, and Dean gave them each one last lazy kiss after they said goodnight. Kissed Castiel first, who kept it short and sweet and still ridiculously hot.

Then Jimmy, who kissed him easy and lavish, lingered much longer than Castiel had, pressed his body tightly to Dean’s. Right up until Castiel tugged him away by the hand and then Jimmy let out another frustrated whine.

As they were walking away Dean heard Castiel say, “Jimmy, stop whining, I’ll let you blow me before bed.”

Jimmy’s whining instantly cut off, and Dean yelled, “That is _so_ not fair.”

Two loud chuckles rang out in the cold air, and Dean grinned at them when they looked over their shoulders at him. Watched them walk inside before he got into his car, that warm feeling in his chest just grew the whole time.


	6. Chapter 6

Breakfast with Dad and Sam went well, seemed to be doing that a lot lately now that Dad’s hours were more regular. Maybe it was that Dean felt less pressure to do everything himself or that Sam felt less neglected, either way, things were going better for them and that made Dean ridiculously glad.

Which sounded really goddamn sappy, even in his own head, but it was true. He hated it when they fought, it always ended up with him refereeing Dad and Sam and then getting accused of taking someone’s side. Wasn’t fair, because Dean tried so damn hard to stay neutral, but it never seemed to matter to Dad or Sam.

But ever since they got here it was like a new leaf, Dad was trying harder, that was easy to see, and Sam was soaking up the attention. For once things were going their way and it felt good.

Once Dean and Sam had thrown the dishes into their crappy dishwasher that only worked half the time, but they all hoped would miraculously save them from actually doing dishes, they’d said goodbye to Dad and headed out to the car.

It wasn’t until they were about half-way to Kevin’s place that it occurred to him the risk he was taking by putting off telling Sam about Castiel and Jimmy. Dean couldn’t think of a reason Kevin would bring them up or their unique relationship. Or more importantly Dean’s involvement in said relationship.

They hadn’t actually _said_ anything to their friends but Dean was sure at least a couple knew about the handjob by now and they couldn’t miss the change in dynamic, even if their touches had been mostly innocent. They were just… closer. But still, definitely a risk. Time to bite the bullet.

“So, uh, Sam.” Dean said extremely eloquently, “There’s something I gotta tell you.”

Sam raised an eyebrow at Dean, “Uh, okay? What’s up?”

Wasn’t that the question though, what was the best way to put this?

“So, you remember, Cas?” Dean asked, that seemed like a good starter.

“Guy with the blue eyes that you were practically drooling over?” Dean cut Sam an irritated look, “What? You were.”

“Ugh. Yeah, him, anyway. So turns out he has a twin and-”

“Dude, twins? That’s like, gotta be a wet dream for you!” Sam exclaimed with a laugh, and Dean flushed. “Oh my god! It _is_.”

Dean chose to ignore Sam’s laughter in favor of salvaging the conversation, “Shut up, Bitch. It’s complicated. Which is what I’m _tryin’_ to explain if you’d be quiet for five damn seconds.” Sam held his hands up in mock surrender. “It’s just...you might hear some stuff from Kevin, just wanna give you a heads up. So, Cas and Jimmy are… unique. They’re, uh, in a relationship. With each other.” Dean paused to let that sink in, “And kinda me, now, too.”

A stunned silence filled the car. Sam blinked at him slowly like he was trying to process Dean’s words, but didn’t fully understand them, “Uh… come again?”

Dean sighed loudly, “I said, Cas and Jimmy are together. And I’m dating them.”

“Wait, but like, they’re brothers…” Sam said, seemed at a loss for words.

“Yeah, but it’s different. I dunno, man. They’re awesome and fucking hot. And it’s totally normal at school. Literally everyone knows and I guess they’ve been like that a long time. Look, I know it sounds weird, but I _like_ them, and fuck knows why, but they like me too, I’m pretty sure. I just wanted to tell you before someone else did.” Dean explained, shrugged and then waited for Sam’s response.

A couple minutes went by and Dean chewed on his bottom lip, gave Sam time to deal with whatever he was thinking.

“So, Dean… You know I like _girls_ right?” Sam finally said with a smirk.

Dean glanced over at Sam with a raised eyebrow before he looked back at the road, not really sure where Sam was going with this but not really liking the look on his face.

“I mean, you’re cute with that girly face and all, but you’re never getting a piece of this.” Sam said with a gesture to his body.

Dean scrubbed a hand over his face, “What the hell, Sam?”

“But, hey, any chance there’s a set of twin sisters hanging around the Novak house? ‘Cause that could be hot.” Sam said with a grin and Dean chuckled as the tension in the car successfully broke.

“Oh, yeah, like you’d even know what to do with two chicks.” Dean teased.

“Shut up, Jerk. I’d figure it out. Heck, I’d just be happy to watch them make out. Oh! Do you do that? Like, hang out and watch while they make out and touch each other and-” Sam asked, ducked underneath the hand that shot out to cuff him upside the head before he sobered a little, “Seriously though, if they make you happy, and you make… them happy? Then I’m glad.”

“Yeah, yeah, whatever.” Dean replied grumpily, but he couldn’t quite wipe the smile off his face entirely even as he watched Sam run up to Kevin’s front door.

It was funny, one of the things Dean kept getting hung up on and that’d made it so hard to tell Sam was the whole comparison thing, brothers to brothers and didn’t that just fuck Dean up a little. ‘Cause if Dean was cool with Jimmy and Castiel then what did that imply about _him,_ or worse _them_? But leave it to that little pipsqueak to smooth past all that with a joke.

When Sam was in the door Dean shifted back into drive and headed out. Castiel and Jimmy only lived about five minutes away but now that Dean didn’t have his conversation with Sam occupying his thoughts he spent the whole time thinking back to yesterday and how amazing it’d been… and how Dean would never be able to give the twins a date like that. Heck, right now he’d barely be able to manage cheap Chinese and bowling.

Still, when he pulled up the drive his wayward thoughts weren’t enough to quell the excitement of spending another day with them. Not to mention he couldn’t _wait_ to see what their room was like. Half of him, the completely twisted half, expected to see sex swings hung from the ceiling and dildos and bottles of lube strewn about. The logical half knew that wouldn’t be the case. Dean was sure they’d put the sex toys away when they had company.

He was still laughing at the thought when he raised a hand to knock on the door. Before he had a chance to make contact the door was swung open.

“Dean!” A wild eyed Jimmy said before he glanced back over his shoulder.

“Jimmy.” Dean replied with a raised brow.

The other eyebrow joined the party when Jimmy quickly stepped out and closed the door behind him, forced Dean to take a step back in order to avoid being pressed against him. Which… But back on topic.

“What’s going on Jimmy?” Dean asked as he started to get concerned. “Where’s Cas?”

“He’s with our parents. Which… Dean I have to tell you something.”

Jesus Christ if Jimmy was about to tell Dean that their parents were in on the action he was turning around now and not looking back.

“They don’t know.”

“You didn’t tell them I was coming over?” Dean asked and tried to puzzle out why that would have Jimmy so worked up.

“Not that.”

“You didn’t tell them about me period.” Dean surmised, a little twinge in his gut.

“Well, no. We haven’t told them about you yet but we figured we’d do it today when we could introduce you. It’s…” Jimmy trailed off, his face twisted with concerted effort.

“Jimmy, just tell me man. Whatever it is-”

“They don’t know about me and Cassie.” Jimmy said in a rush.

Dean stood there in stunned silence for a moment.

“H-how do they not know? _Everyone_ knows. The other kids at school, the faculty. You guys don’t exactly hide it.” Dean said without a drop of malice in his voice.

“It’s… So, we’ve had a few teachers over the years that suggested splitting us up. One even succeeded in convincing our teachers to rearrange our schedules, so same teachers but not at the same time. We… we were a mess. We were always just _better_ when we were together. We balanced each other. So when our parents figured out the issue they fixed it.” Jimmy paused to gather his thoughts, gave another glance toward the door.

“A few years ago a teacher… they suggested that maybe Cassie and I should split up again… that we were too close. I guess our parent’s remembered the way we were when we were split up before so they said no way. But the teacher pressed, tried to insist. Even suggested maybe we should see a psychologist. Then our parents _suggested_ that maybe this wasn’t the right school for their sons _or_ their money. They’re the largest yearly donor to the school. After that, the teacher never said a word to us and I’m betting the rest of the faculty got the word to keep their traps shut or it would be their job.”

Dean did his best to process all that, surprised to learn that he’d been at least a little right about money being part of the reason no one gave Jimmy and Castiel crap about their relationship.

“How the hell did you find all that out? Did your parents ask you about it?” Dean asked as he anxiously shifted; he felt a little exposed standing out front for so long like this.

“Oh no. We paid someone to hack our records freshman year.” Jimmy said with a distracted wave.

Dean opened his mouth to ask how things worked at home but he was interrupted as the door opened and a nervous looking Castiel stuck his head out.

“Jimmy, Mother and Father are wondering what you’re doing out here. Hurry up!”

“All set Cassie!” Jimmy said, grabbed Dean’s arm and dragged him into their home.

With all that lead up Dean expected some sort of introduction, some weirdly formal thing where he was presented to Mr. and Mrs. Novak. What he got was escorted quickly through the foyer and up the stairs with nothing more than a, “This is Dean, we’ve got homework.” shouted over Jimmy’s shoulder as they booked it up the stairs, Dean in tow.

“Guess I’m getting the penny tour.” Dean laughed as they finally slowed on the second floor landing.

“Oh, sorry Dean, we… we’ll give you the tour later.” Castiel said, clearly a little distressed about having forgotten his good manners in his excitement to have Dean there.

“Our wing is the best part of the house anyway.” Jimmy said with a grin.

Their… wing?

Dean figured that they would have separate rooms, since their parents were oblivious, but a whole wing just to themselves? Sam and Dean had only just gotten their own rooms for the first time at their new place and both were barely more than closets.

Dean followed the twins down a hallway that had three doors, one at the very end and two that mirrored each other on either side of the hall.

“Those are our rooms, we’ll show you those in a bit, but first our playroom.” Jimmy said as he gestured at the two doors before he walked to the door at the end.

For a heart stopping moment Dean was sure that he was about to walk into some padded room full of sex benches, chains and whips. Instead he walked into a teenage boy’s wet dream.

It was a large room that ran the length of the side of the home, walls in one corner built out to make a small room, likely a closet or maybe a bathroom. The three exterior walls were lined with floor to ceiling windows with only one large gap in the middle of the wall across from the door where an enormous entertainment center sat. It had the biggest TV Dean had ever seen outside of a movie theater and the shelves below it housed what looked like every gaming system known to man.

In front of the TV was a sort of lounge area with a long, overstuffed couch bookended by two matching arm chairs that looked easily big enough to fit two people. In front of the couch, the floor was covered by the softest looking carpet and Dean was immediately struck by the image of Jimmy and Castiel sprawled out on their stomachs as they played video games. And maybe the image devolved into the two of them rolling around on said carpet, but wasn’t like anyone would know.

A glance around and Dean spotted recessed speakers all around the room, no doubt they created an incredible surround sound. Shelves and cabinets lined the interior wall that the entrance was on, along with two other doors that were recessed into the storage.

If Dean was drooling over the entertainment set up he was practically weak-kneed when his eyes moved over to the left of the room and he spotted the pool table. It was clearly high end, with dark wood polished to a high shine and thick tooled legs.

He hadn’t even finished taking everything in, and he suspected that the things that were visible were only half the story, when he heard the door click shut. Dean turned to see Jimmy leaned against the door while he looked at Dean pretty much the same way he'd eyed the burger he’d inhaled last night. Dean’s cock thickened a little in response, and he thought he definitely had something else he’d be happy to let Jimmy put in his mouth.

Unfortunately, just as Jimmy pushed off the door a voice rang out.

“Jimmy, we talked about this. We’re here to work.”

Disappointedly, Jimmy glanced over at Castiel with a pout before he walked to the couch and threw himself down on it. Castiel merely rolled his eyes before he went over to one of the doors Dean hadn’t been through and picked up his backpack which had been set on the floor nearby. For the next hour Dean and Jimmy listened as Castiel read through the chapter that their project was based on and they discussed how they were going to go about it.

They’d all started out sitting on the couch, Dean bookended by the twins, but at some point Dean had shifted enough that he was leaning with his back pressed to Castiel’s side. Jimmy had made a much more noticeable transition and was laying with his legs draped over the arm of the couch and his head resting in Dean’s lap. Valiantly, Dean resisted his urge to run his fingers through Jimmy’s hair as they debated whether to do an in person demonstration or just make a trifold poster with visuals to represent the experiment and their results.

Of course when Castiel suggested Jimmy just wanted to do the demonstration because it meant they wouldn’t have to do as much work _today_ , Jimmy sat up and leveled an indignant glare at Castiel. Mostly Dean was just sad that he hadn’t given into the urge to touch Jimmy’s long soft locks and now it was too late. Still, he wanted to stave off what sounded like it was gonna devolve into a full blown argument.

“Why don’t we do some of both?” Dean suggested carefully.

After a pause both twins spoke at once.

“I’m listening.”

“Go on.”

“Well, we should run the experiment a couple of times anyway, just so we know we got everything right and can count on the results. So we do that, take some pictures, and chart the results. Slap it all on some poster board and we got ourselves a visual aid for when we do the live demo.” Dean said.

The look on Jimmy’s face as Dean increased their workload made it clear that Castiel was totally right about his brother’s thought process. Since he’d been so pissy about Castiel suggesting it though Jimmy couldn’t argue against it.

Dean was just happy that it meant he had an excuse to stay even longer.

An hour later they finished the lunches that Castiel had called down to the kitchen to have brought up (seriously guys, it’s not that far, we can just go d-okay nevermind) while Jimmy destroyed Dean in the latest GTO.

Castiel stood and started to sort through the supplies for their project that had come up with the lunch order while Jimmy and Dean begrudgingly put their controllers away.

Surprisingly, the three of them managed to stay focused on the work for the next few hours. Just as they put the finishing touches on their poster, the door to the hallway opened and the twin’s mother poked her head in.

“Your father and I ended up deciding to stay home tonight so we’ll be having dinner together. At the table. In the dining room. Like civilized people.” Mrs. Novak eyed the remnants from lunch still littered about the carpet. “Get cleaned up and dressed for dinner and we’ll see you downstairs in half an hour. You too Dean.”

“Oh, umm, that’s okay Ma’am. We’ve finished up so I’ll just leave you to your family dinner.” Dean said hurriedly as he plucked his jacket from the chair he’d tossed it on earlier.

“Nonsense, I’m sure at this hour your family is already expecting you to be out. No need to run off just because _boring_ Mom and Dad are sticking around.” Mrs. Novak said with a grin that was way too cheesy for someone as high class as she was.

Huh, even loaded parents could be dorks.

“Really, it’s okay. I’m not even dressed for dinner.” Dean said as he self-consciously smoothed his hands over his worn band tee and faded jeans.

Mrs. Novak looked Dean up and down before she stepped into the room and hit the intercom button just inside the door.

“Yes, Sirs?” A female voice sounded from the speaker.

“Magda, it’s Mrs. Novak. Please come up and bring Dean to Mr. Novak’s dressing room. Help find him something to wear for dinner.” Mrs. Novak released the talk button and turned to Dean to look him over once again. “You’ll have to keep your own pants but there should be a shirt and tie that will fit you well enough. Jimmy. Castiel. Go.”

Both Jimmy and Castiel hesitated over leaving Dean but a look from their mother had them rushing to the doors on either side of the hall entrance. Cleared up that mystery at least. Dean had assumed the doors were more storage but evidently they led to the bedrooms.

He contemplated following one of them to see what their room looked like, had to be pretty big considering how far down the hall the other doors were, but couldn’t decide which one to follow. Before he could make up his mind a short older lady in a maid's uniform appeared in the doorway that Mrs. Novak had evidently vacated.

“Mister Dean?” She questioned, her hand out to escort him.

“Oh, umm- just… just Dean is fine.” Dean stammered as he went with her.

A half hour later Dean stood outside the dining room wearing a pressed white dress shirt that was just the acceptable side of too tight and a dark red tie that made him feel like he was walking into his execution with the noose already around his neck. Inside, he could hear the Novak’s as they talked and laughed. Softly, of course, dignified and civilized.

Dean knew he should go in there but he’d seen this enough in movies to know what to expect. The new boyfriend comes around for dinner and get’s the third degree. Except he didn’t know what to say when they asked how Dean knew Jimmy and Castiel. What if they asked if he was dating one of them? Did he just… pick at random? Lie and say no?

Oh shit. Did they even know that Jimmy and Castiel were into dudes? If they’d only ever been with each other and their parents didn’t know about them then it was likely they had no idea. On the one hand that meant that they likely wouldn’t question whether or not Dean was anything more than a classmate. On the other, what if he accidentally outed them?

Dean was so stuck in his spiraling thoughts that it took him a second to realize that the conversation had stopped in the other room.

“Dean, sweetheart.” Mrs. Novak called, “You can come in. We won’t bite, I promise.”

Cautiously, Dean peeked around the open double door and found four sets of eyes on him. He inched into the room and did his best _not_ to look like a deer caught in headlights. He shuffled in sheepishly, and took in the room as he did.

It was massive, complete with crystal chandelier and all. Dean quickly got the feeling that they had a different set up when entertaining people though because instead of a long fancy table that fit the size of the room there was a smaller one that had just enough room for the two heads of the table and two chairs on each side, though currently there was only one chair on one of the sides. Mrs. Novak must have noticed him looking at it.

“Oh I’m sure you’re used to a much bigger table but when it’s just family we prefer a smaller setting to allow for more comfortable interactions. Actually, it’s usually slightly smaller but we added in a leaf so you wouldn’t have to sit in someone’s lap.” Mrs. Novak said with a laugh.

Of course Mr. and Mrs. Novak were seated on either end. Jimmy and Castiel sat on the same side and the empty chair was set dead center on the other side. Dean wasn’t sure if they’d only put one chair in because that was all they needed or not but he was glad not to have to choose which parent to sit closer to.

Dean took his seat and soon after dinner was served. It might’ve been a less formal setting but that didn’t make the meal any less extravagant. Fortunately, Dean managed to get through the first course in silence as Mr. and Mrs. Novak discussed plans for the following week. He was thrilled to just blend into the chair with nothing of worth to contribute to the conversation.

His luck ran out just when he put a bite of the most perfect lobster ravioli in butter sauce that he’d ever had in his mouth. Okay, so the bar wasn’t exactly high for that since he’d never had it before but still, it was pretty damn good. He didn’t get to enjoy it long as it suddenly turned to paste in his mouth when Mr. Novak addressed him.

“So Dean, how do you know the boys?” He asked before he took a bite of his food.

As he tried to force the bite down his throat, Dean was pretty certain he was going to end up choking and dying. Which, hey at least he wouldn’t have to answer.

Honestly, he didn’t know what the answer was. Just a school friend? Lab partner? What had the boys told their parents this morning? Or yesterday? Did they even tell their parents where they were going? Does he say he’s dating them? Which one? Would picking one to toss out there hurt the other’s feelings? Was he about five seconds away from blurting something that would end up outing the twins to their parents?

“He’s our boyfriend.” Castiel answered casually between bites.

“Oh, that’s wonderful! I’m so glad you boys are finally dating! Especially you Castiel, you work far too hard.” Mrs. Novak said as she smiled warmly at her sons.

“Mother.” Castiel said and Dean was amazed to see color had flooded his cheeks.

“She’s right Castiel. Hard work is important but so is taking time to enjoy yourself. As for you Jimmy, perhaps Dean will help you find a little discipline, give your brother a break from having to keep you in line.” Mr. Novak said jovially.

That time Dean really did choke as images of Jimmy bent over and getting spanked with a paddle by Castiel before he turned and handed it to Dean suddenly swam in his head. When he finally managed to clear his throat after copious amounts of water, the table settled back down, moved on from the subject.

“So Dean, did you notice how large the property is and how much of it is wooded?” Mr. Novak asked casually. “Also, unrelated did the boys show you my extensive collection of hunting rifles yet?”

“Dad!” Both twins shouted in unison.

“He’s just kidding Dean.” Mrs. Novak said with a  glare at her husband before she deadpanned back at Dean. “The rifles are kept at his hunting lodge of course and there’s _much_ more land there.”

Wide-eyed, Dean just stared at her for a moment. Then the room was filled with the sound of Jimmy and Castiel groans and their parents laughter. Thankfully, the exchange broke the tension and Dean was able to enjoy his meal.

“So what are you boys doing now? You’ve finished your project?” Mrs. Novak asked as the last plates were cleared away.

Jimmy looked like he was about to say something but Dean got there first.

“Actually Ma’am, I’ve really got to be goin’ now. Got school tomorrow so I gotta get my little brother home and make sure he’s got his homework done. Not that he really needs it, probably finished it on Friday.” Dean said and suppressed the proud grin that was threatening.

“That’s very responsible of you Dean.” Mrs. Novak said with a concerned raise of her well manicured brow. “May I ask why your parents or the nanny don’t do that?”

Dean’s supper started to revolt in his stomach when he realized his slip.

“Oh ummm, it’s just our dad, Ma’am.” Dean struggled to answer in a way that wouldn’t leave him totally humiliated at best and kicked to the curb as not good enough at worst. “Mom died when we were little. Dad has to be up at four for work so he goes to bed pretty early ‘n he prefers family watchin’ over Sammy to strangers.”

Dean hoped they wouldn’t take offense at the last bit. He already knew that the twins had had a nanny when they were younger.

“I’m sorry to hear about your mother, sweetheart.” Mrs. Novak said softly before she reached over to cover Dean’s hand with her own.

Completely taken off guard by the unexpected tenderness directed at him by a woman who barely knew him, Dean just looked at the table.

“I hate when I have to get up so early for overseas calls. The base of operations is here, calls should be scheduled around _our_ time.” Mr. Novak burst out.

All of the tension in Dean left him once again and it wasn’t long before Jimmy and Castiel were walking him out the door and to his car, hands in his. When they got to Baby, for the first time Dean was disinclined to slide down into her smooth leather interior.

“Hey, I had a lot of fun today guys. Kinda surprised since we mostly just worked on the project.” Dean said as he reluctantly released their hands.

“Didn’t even get to show you our bedrooms.” Jimmy said with a pout that shot straight to Dean’s groin.

“Jimmy, I’m pretty certain that nothing you would want to do in the bedroom is something that occurs after just one date.” Castiel said in an attempt to be stern but wasn't able to suppress the affection and maybe a little bit of want from coloring his words.

Dean opted not to point out that half the time he didn’t even make it _to_ the first date, or even the bedroom in most cases. There was something he was curious about though.

“So, uh… two bedrooms huh?” Dean said, looked down as he toed at the ground. “Kinda expected it to be one big bedroom for the two of you. Maybe a cute little set of bunkbeds.”

“We’ve always had our own rooms, at least since we left the nursery. Of course we would just sneak into one another’s room after we were tucked in. Our parents and the nanny eventually stopped trying to get us to stop. When they remodelled our wing we requested the lounge area be connected to both rooms for ease of access. Our parents just didn’t realize the ease of access was to each other and not our games. So now we just make sure both sets of bedding appear used for the staff and our parents think we’ve outgrown a childhood comfort.” Castiel finished.

Dean nodded.

“But if you’re asking if we fuck each other silly each night before curling up and falling asleep together in a big pile of sweaty, slick skin, then the answer is: of course.” Jimmy said with a lopsided grin.

“Jimmy.” Castiel chastised but his expression was one of fondness and heat.

“Yeah, about that. What with you guys being hush hush around your parents I was kinda surprised when you told them I was your… boyfriend. They didn’t even question you two dating the same person.”

“Oh that. We have an aunt that has a husband and a live in boyfriend. That’s just the one related to us. People stopped being scandalized by polyamory and open relationships the second it became _fashionable.”_ Jimmy said.

“Besides, we’ve always shared everything else, even when Mother and Father would try to treat us as separate people, why would we stop now?” Castiel asked with a smirk before it melted into uncertainty. “Or perhaps it was my use of the term boyfriend that you questioned? Because I just threw out a label. Old people love to label everything.”

“Hey,” Dean said and reached out to hook Castiel’s pinky with his own. “I wasn’t questioning _that._ ”

The three of them stood there quietly for a beat, pleased smiles on all of their lips.

“On that note.” Dean said, then pushed off of the car he’d been leaning against. “Does one date get me more kisses goodnight?”

“Of course.” Castiel said.

Dean flashed a grin then leaned forward to brush their lips together. Last night’s kisses had been soft, lazy, tired. This one… this one made Dean's mind go blank as Castiel’s lips pressed into his, hard and demanding. Then his tongue pressed for entrance and Dean was powerless to deny, every braincell flooded with pleasure as Castiel took what he wanted before he pulled away.

That wasn’t at all what Dean had expected from calm, proper Castiel.

While Dean stood there, eyes half closed and lips still parted his haze was pierced by someone awkwardly clearing their throat a couple of inches from his face. Dean opened his eyes fully and straightened up quickly.

He looked over from Castiel’s face to his left where Jimmy stood with a forced smile on his face as he looked just beyond Dean. He must’ve been out of it longer than he thought after that kiss, long enough to maybe plant it in Jimmy’s head that he wasn’t gonna get kissed goodnight. Which was fuckin’ ridiculous because no way would Dean forget him like that.

“C’mere you.” Dean murmured as he reached out, hooked the back of Jimmy’s neck and pulled him in.

When Dean pressed his lips to Jimmy’s he felt the corners of Jimmy’s lips curl just a bit in a content grin. Suddenly, Dean wanted to taste those curves, to see what Jimmy’s happiness tasted like. He traced each line and bend before he let just the tip of his tongue dip between Jimmy’s lips. Then he pulled away and Dean was content to see Jimmy’s face mirrored what his own must’ve looked like after Castiel'd kissed him.

Softly, Dean brushed the ridge of Jimmy’s cheek with the pad of his thumb before he turned and got into his car. Then he waved in his rearview as he watched them come together to wrap an arm around each other while they waved back. Dean smiled and for a brief moment his mind tried to separate the two of them, tried to imagine ending a date with _just_ a strong, dominating kiss or _just_ a soft, giving kiss and it just wouldn’t happen. The idea of dating only one of them wouldn’t even compute anymore.

Which was why it was all the more important that Dean not fuck this up, that he give them everything they deserved. Being in their home only solidified that he couldn’t do that as things were now. When his thoughts took a dark ugly twist, told him that he wasn’t good enough and never would be, he shoved them away.

No. He’d just have to make sure he _did_ deserve them.

With his shoulders set, Dean headed to Kevin’s house his thoughts firmly resolved.


	7. Chapter 7

It didn’t take Dean long to find some under the table jobs on craigslist, and by not long, Dean meant he found some to start Monday after school. Just manual labor for some rich people who lived close enough to school that he could work between when he got out and when he needed to pick Sam up and then a couple more after he dropped Sam off at home. Sure, it meant he’d be busy, but it was nothing he couldn’t handle. And besides, it’d be worth it.

Monday wasn’t so bad aside from the fact that he was a little tired and sore when he got home. Kinda sucked that he didn’t really have the energy to text with Jimmy and Castiel like he normally would’ve, though. Just enough left in his reserves to do his homework. Had to be a good example. Despite that, he slept well that night when he fell into bed just after he’d sent them a goodnight text.

Tuesday was a little rougher, his alarm went off way too soon for his liking, he ended up taking too long in the shower and nearly made Sam late for school. Which he would probably never have heard the end of. Luckily they’d gotten there just in time so Dean’d been spared.

He worked the same houses he’d been working the day before, and while the work was mind-numbingly simple, it was a bit of a workout and in spite of the cold weather, by the time he left the last house he was fairly sweaty and gross. He didn’t even wanna pull on his jacket, so he just slung it over his shoulder and trudged to his car.

Wednesday was when fatigue really set in, but Dean just pushed it down and tried to act like he was fine. He was distractible as hell in class, barely kept it together enough to scrape by, and at lunch he only managed to pay just enough attention to keep up with everyone. At the end of the day when Castiel asked if he wanted to come over and study, Dean had regretfully requested a raincheck while Jimmy frowned a little, which just made Dean feel worse.

He’d planned to ask them out tomorrow, but that look on Jimmy’s face was killer, and he wanted to see him smile, so he walked them to their car, and asked them out to dinner on Saturday. Jimmy’s grin as he said yes was exactly what Dean needed to help him get through the rest of his afternoon and Castiel’s little warm smile while Dean kissed him then Jimmy was a bonus.

Thursday and Friday were a blur of exhaustion that Dean barely managed to push himself through. He really missed having time to text with Castiel and Jimmy. That’d been probably the hardest part about his sudden lack of time, and he knew they had to have noticed the marked drop-off in the the length and frequency of his replies.

Hopefully Saturday night would make them forget all about it though. He just had a few jobs to get done that day before he went home and showered. He’d manage to make enough that he could afford to pick up a really nice like new used black suit that fit him fairly decently along with having enough to comfortably pay for dinner at the same fancy place they’d picked up the gelato for Jimmy from.

Meticulously, he’d studied their menu online to make sure there was actually something he could a) pronounce and b) would want to eat. The added benefit of that was that it left him extra familiar with exactly how much supper was likely to cost and thanks to all the hours he’d been working he’d have money to spare.

Which came in handy when he booked the reservation and requested their most private table. He wanted Jimmy and Castiel to feel comfortable, and when he and Castiel had dropped in that time he’d noticed the little table toward the back that was basically walled off by tall half-walls topped with lush plants. Enough privacy that no one would really be able to see what was going on. Pretty much one of the reasons he’d chosen the place. Plus he already knew Jimmy, at least, would like it.

That Saturday, his morning dragged on, but he kept reminding himself that in a few hours he’d get to see Jimmy and Castiel. Even if by the time he got home, and showered he was pretty damn exhausted. Didn’t help that the suit wasn’t something he was used to at all. Or that Dad’d basically given him the silent ‘What are _you_ up to tonight’ look when he’d rushed out of the house.

Dean tried not to think about the fact that at some point he was gonna need to figure out how the hell to tell _him_ about Castiel and Jimmy. His brain just didn’t even wanna consider _that_ awkwardness. He doubted very much that Dad would take it as well as the Novaks did. Once he’d slid into the car he tugged on his tie, loosened it a bit and figured he could fix it up when he got there.

The drive went by pretty quickly and before he knew it he’d pulled up to their house and parked. A little nervous, Dean jogged up the front steps and knocked on the door. Right as it opened, he snugged his tie back up and tried not to fidget.

After that he forgot about being nervous because Castiel was standing there in a fitted charcoal grey suit with a white dress shirt that fit him like a glove, and a thin light grey tie, add to that a tiny little smirk on his face while Dean checked him out and _Jesus,_ no wonder Dean’s brain wasn’t functioning anymore _._

Right next to him was Jimmy, and Dean let his eyes travel over Jimmy’s body just as slow. In his navy blue suit, jacket unbuttoned to show off a matching pinstriped waistcoat that accented his slim waist and a blue tie, with just a hint of color from his purple pocket square, Jimmy looked fucking gorgeous too.

“Wow.” Dean said when he finally regained the ability to speak, “You guys look… yeah, wow.”

So his brain still had trouble functioning, who could blame him?

“You look great too.” Castiel said, and Dean was cognizant enough to notice when Castiel’s eyes dropped to give him an elevator look.

Then Jimmy stepped forward and reached out to wrap Dean’s tie around his hand, pressed his body right up against Dean’s, “I like you in a tie. Reminds me of how much I enjoy watching you at school in your uniform. And the things Cassie and I have talked about using _that_ tie for.” _Holy fucking shit,_ Dean was pretty sure like ninety percent of his blood just made a mad dash south. “Stuff we want to do-”

“That’s enough, Jimmy.” Castiel warned, “I’d like to actually make it to the restaurant.”

After a quick flash of a predatory grin, Jimmy stepped back, let Dean’s tie slip between his fingers with a weak glare back at Castiel and a muttered, _cockblock,_ under his breath.

All three of them ended up squishing into the front seat of the Impala, Castiel in the middle and Jimmy on the outside, because Jimmy said he’d get carsick if he didn’t get the window seat. Dean suggested there’d be more room for them in the back, but they’d both shrugged and slid into the front anyway. Not like Dean was gonna complain about Castiel being pressed up against his side for the drive.

At least it gave him something to take his mind off the nervousness that was fluttering in his stomach. Aside from the food he’d eaten at the ski lodge, which for the record had been before he’d known how much it cost, this was going to be the most expensive place he’d been to. And the fact it was on a date, well that just added to the pressure.

He tried to shove down any reservations he had before they got there, because it was the sort of place Castiel and Jimmy were used to and they had no idea that _he_ wasn’t and Dean wanted to keep it that way. He _already_ didn’t deserve them, Dean didn’t need to go around showing them just how _much_ he didn’t.

So when they parked in front of Scalini Fedeli, Dean was all smiles while Jimmy gushed about how much he loved the place. Dean didn’t point out how he’d known but when they got out of the car, Castiel leaned in to whisper how sweet it was that he’d remembered in Dean’s ear. Warmth curled in his chest at the praise and his cheeks heated a bit, but Dean just smiled and opened the door to the restaurant for them.

The hostess was pretty fast on her feet and got the three of them to the isolated small square table Dean had booked without much of a wait. Dean wound up on one side of Castiel while Jimmy was on his other, but the table was pretty small, so it didn’t feel like much distance between any of them. As Castiel and Jimmy sat down, Dean quietly offered the hostess a pretty generous tip to make sure they were bothered as little as possible and for discretion, as well.

After that they slipped into quiet conversation while they waited for their drinks, and at least that part Dean found easy, because after this long, talking to Jimmy and Castiel was like settling into something warm and familiar. Jimmy talked to Dean about a videogame he wanted to play with him and Castiel talked to him about their schoolwork, and suddenly Dean realized that all of their attention was on him.

Kinda like they were both on separate dates with him, not really interacting with one another much and Dean wondered if it was because they were worried about being together in public.

“Guys?” Dean said, and when they both looked at him questioningly, he continued, “Listen, I made sure no one was gonna bother us unnecessarily and when they do they’ll know to be, ya know… discreet. So, it’s, uh, it’s okay to be _you_ tonight.”

Jimmy beamed at him, Castiel’s eyes went a little soft and warm and Dean’s heart rate picked up a bit when they shifted closer to each other, like they were relaxing. Just like he wanted them to be able to.

“Thank you.” Castiel said quietly to him and Jimmy happily echoed it.

A few minutes later the waitress came, dropped off their drinks and took their orders. Dean had already picked what he wanted, and Jimmy and Castiel were familiar enough with the restaurant that they’d barely glanced at the menu. Eventually their conversation turned to their plans for spring break when Castiel asked Dean what he would be doing.

“Uh, nothing, I don’t think. Just hanging out at home mostly.” Dean said before he realized that probably wasn’t the norm for affluent private school kids. He shifted uncomfortably in his seat before he redirected them, “Why? What d’you guys usually do?”

“Go somewhere warm and tropical.” Jimmy answered with a grin and Dean offered him a stilted smile, because of course they did. Which meant pretty soon, Dean was gonna be left on his own for a whole week, and if that one weekend after he’d met Castiel had left him feeling lonely, he could barely imagine what he’d be like after a full week without them.

Instantly, Castiel seemed to notice Dean’s melancholy and interpreted it partially correctly, “Of course, this year we thought we’d stay home too. Our parents will mostly be gone, and we thought you could spend it at our house.. if that's something you’d like…”

Dean’s lips pursed a little, “Cas, it’s not that I don’t want to, but you know you guys don’t gotta stay here for me, right? Like, if you always go down south and you like doing that, then you should. I’ll be fine.”  Probably.

“While I appreciate your concern, we already decided to stay, didn't we Jimmy?” Castiel said with a pointed look at him.

“Oh, yeah. Absolutely. Who needs sunshine when we could be here with you having hot s-”

“That’s _not_ the only reason.” Castiel said quickly, like Dean wouldn’t have paid good money to hear the rest of Jimmy’s sentence.

“Yeah, of course not.” Dean said with a smirk, “But it sounds like a hell of a perk to me.”

Shortly after that, their meals were delivered and all three of them got caught up in eating their food, which meant conversation died out a little, but the groan of enjoyment Jimmy let out when he took a bite of his fettucine alfredo was totally worth the lull in conversation. And although Dean felt out of place in the fancy restaurant, he could still admit his pasta was phenomenal.

Some of Dean’s nerves melted into the warm glow he felt each time Castiel laughed at something Jimmy said. When Jimmy leaned in to brush a quick kiss across Castiel’s lips. And how Castiel would twine his fingers with Dean's whenever he wasn't eating. While it didn't erase the feeling of not belonging, it damn sure made Dean wanna fake it the best that he could.

Midway through desert, Dean's adrenaline and nerves finally wore off, and his exhaustion from working earlier set in a bit which made him sort of quiet. Could’ve been blamed on being stuffed full, or the delicious panna cotta with raspberry coulis that Castiel had recommended for desert, but Dean was just dead tired. Dutifully, he tried to keep up with the flow of topics, but he was a bit more subdued and when Jimmy and Castiel started discussing their plans for tomorrow Dean kinda zoned out.

‘...Dean?” Jimmy’s voice finally broke through just as his hand closed over Dean’s. After a quick blink Dean looked up at him curiously.

“Oh, sorry, just, uh, didn’t sleep well last night.” Dean lied, sort of poorly for someone who normally thought of himself as a pretty good liar.

“Did something happen?” Castiel asked, concerned, while the hand closest to Dean gently gripped his thigh.

“Oh, uh, no. Just… guess I was nervous?” Dean went with a half-truth, because he _was_ nervous.

“Aww,” Jimmy said warmly as he reached across the table and laced his and Dean’s fingers together. “That’s cute.”

Warmth flooded Dean’s cheeks and he rolled his eyes, but Jimmy just chuckled and Castiel grinned at them. Until the waitress walked over and Jimmy reflexively dragged Dean’s hand under the table in a practiced motion that kinda made Dean’s chest ache. That kind of instant reaction was clearly the result of years of hiding.

Underneath the table Jimmy went to pull his hand away, but Dean tightened his grip reassuringly. Stroked his thumb over the smooth skin of Jimmy’s index finger. The waitress left the bill and told them to take their time, and Dean smiled and thanked her. Almost the second she walked away Jimmy’s eyes fell on Dean’s and a little smirk tugged the corner of his lips. Dean swiftly realized that their joined hands were resting in Castiel’s lap.

Didn’t seem to be bothering him though because he was still slowly eating his panna cotta like he hadn’t even noticed the sudden weight of two hands on him. Jimmy, however, definitely noticed. Slowly, he slid his hand around so that Dean’s hand was palm down on Castiel’s lap with Jimmy’s covering the back of it.

At the same time that Jimmy started to push Dean’s hand down in a slow grind against Castiel’s dick, he shifted to slide his foot up the inside of Dean's calf in a tease that left Dean achingly hard way too fast. Castiel's cock wasn’t far behind, and Dean kept his eyes on Castiel's flushed cheeks and hazy eyes while he and Jimmy gradually increased their pace over the soft material of Castiel's pants. So damn hot like that, Castiel bit his lower lip and dragged it through his teeth.

And it was so fucking hard for Dean to resist leaning in and chasing those teeth marks with his tongue, but he didn’t wanna break whatever spell was keeping Castiel from slowing them down. Finally though, Castiel came back to himself when his hips involuntarily pushed up against their hands, and he snapped out of it.

With one last shaky breath, Castiel covered Jimmy's hand with his, stopped them, “If you two keep it up I'll have to make you both come in your pants right here. And Jimmy can tell you from experience how uncomfortable sitting around in come filled underwear is.”

Briefly, Dean thought that might be worth it because his cock throbbed with need. Jimmy raised an eyebrow at Dean and he almost, almost pushed Castiel, but then Castiel's lips pinched together and Dean knew that wasn’t how Castiel wanted things to end up, so he shrugged apologetically at Jimmy and took his hand back.

A wry smile spread Castiel’s lips, “Smart move, Dean.”

They all took a few minutes to calm themselves down and finish off the last of their drinks before Dean took the bill and placed the cash to cover their meals along with a decent tip inside the folio, the last of a week's worth of hard earned money, then set it back on the table. Dean stifled a yawn as he stood and then led Castiel and Jimmy out of the restaurant and into the wintery night air.  

On the ride home the car was fairly quiet, with just the hum of quiet rock music filling the silence. Castiel was squashed in the middle again, and he’d laid his head lazily on Dean’s shoulder as they drove. Jimmy was staring sleepily out his window, and Dean was quietly mumbling along with the music in a bid to keep himself awake.

Abruptly, Jimmy sat up straight while he jabbed a finger toward his window, “Look! Guys, can we stop?”

Dean glanced out the window to see what the heck Jimmy was so excited about, and had to admit, it was pretty fuckin’ sweet; A huge frozen over pond surrounded by a winding walkway, everything covered in a sparkling layer of snow that the full moon lit up. Looked like something right out of a Christmas movie.

“Please? Let’s just go for a quick walk, it’ll be fun!” Jimmy said all excitedly, and there was no way Dean was gonna be able to say no to that face, so he turned onto the road that led to a parking lot.

“But we don’t have our winter jackets.” Castiel objected. “And it’s freezing.”

“Aww, come on, Cassie. A little cold isn't gonna hurt.” Jimmy countered and Castiel looked up at the ceiling annoyed before Dean interrupted. 

“I got a couple ‘a blankets in the trunk with my winter emergency kit. If we wrap ‘em around all of us, they’ll heat up pretty quick and keep in the warmth.”

“I suppose that’s an acceptable solution to our problem.” Castiel agreed a little reluctantly.

“Cassie hates to be cold.” Jimmy stage whispered to Dean.

Dean’s eyebrow quirked as he put the car in park, “Uh, so why skiing then?”

“Because that’s different.” Castiel said. “Between warming up from exertion and full snow gear, it’s not _that_ cold. Not like walking around with just a suit jacket in the middle of winter.”

“Hmm,” Dean considered, “Why don’t you be in the middle then? Me ‘n Jimmy can keep you warm.”

“Yeah, we can.” Jimmy agreed just a touch of a dirty smile on his face and Castiel chuckled.

“Okay, fine. Let’s do it.” Castiel capitulated.

“Yes!” Jimmy exclaimed.

Dean grinned at the two of them fondly, “Gimme a sec to grab the blankets.”

With that, Dean climbed out of the car and popped the trunk. He rummaged around until he found the blankets he knew were in there and gave ‘em a little sniff test. The results of which were decent, though a little like they’d been in the trunk too long. Honestly, he should chuck them in the wash next time he needed to do laundry in case this happened again. Oh, well, they’d work.

So Dean pulled them out all the way and closed the trunk. By the time he’d gotten up to the passenger door, Jimmy had already opened it up and and was getting out. Castiel followed and Dean quickly stepped up next to them and slipped the blankets around their shoulders.

Dean’s hand brushed over the small of Castiel’s back, and found Jimmy’s already there.  He quirked a smile and tangled their fingers together. Once the blankets were securely snug around them, they walked along the path. Everything was still and so quiet, the middle of winter and nothing around to hear but the sound of their breaths puffing clouds around their faces.

And all cuddled up like that, with Castiel between them, Jimmy’s hand warm against his, Dean just thought it was all worth it. Running himself ragged, the exhaustion, he’d do it all over again, would _keep_ doing it because this, with _them…_ was everything.

Castiel’s hands slipped into Dean’s and Jimmy’s free ones, and Dean’s heart sounded loud in his ears, he wondered if Castiel could feel it through his hand while a warm, tender, feeling grew big in Dean’s chest. The moonlight on the snow, and the silent stillness of the place, that was beautiful, but Castiel and Jimmy? They were _perfect._

“How ya doin’ there, Cas? Warm enough?” Dean finally asked just to get out of his own thoughts.

“Mmm. Perfectly.” Castiel said softly. “You were right, Jimmy, this is nice.”

“Woah, wait, what?” Jimmy said with pretend shock in his voice, “Did Castiel Novak, _the_ Castiel Novak, just admit that _I_ was actually right about something?”

“Don’t act so shocked.” Castiel said dryly. “It’s not as if it’s the first time.”

Jimmy shook his head and shot Dean a masterfully executed sad puppy look, “He’s lying Dean, it’s absolutely the first time he’s said that to me.”

Dean opened his mouth to reply but Castiel got there first, “What about that time that you insisted on crossdressing for me? I honestly thought I wouldn’t like it at first, and I admitted you were right. That mini skirt and those lacy panties looked extremely hot on you.”

To Dean’s credit, he only stumbled a little there when his dick took sudden intense interest in the conversation.

“Yeah, yeah, fine. So he’s said it once before.” Jimmy admitted with a grin. “Sometime we’ll have to show you just how much he likes it.”

“Hell yes.” Dean agreed fervently, not that he’d fantasized about Jimmy in a skirt since his off-hand comment at the ski lodge or anything. Definitely not multiple times. Nope.

The rest of their walk wasn’t as talkative, partly because it was getting late, and Dean was still barely keeping himself on his feet, and partly because they all got lost in the contentment of walking together. Eventually they turned around and headed back to the car.

When they got to Jimmy and Castiel’s house, Dean hopped out of the car and followed them to their door despite his general drowsiness. He might not’ve been on many real dates, but he’d been on enough to know that you walked your date to the door and made sure they got in safe. Not that that was really an issue in their kind of neighborhood, but still.

“Wanna come over tomorrow for a bit?” Jimmy asked hopefully before he hurried on to cut off the warning that was already forming on Castiel’s lips. “Cassie has to go with Mother to some lunch thing, drew the short end of the stick on that, but we could play some more Gears of War until he gets back then watch some movies or something. Nothing hinky.”

“I'd love to but I promised Sammy I'd help him with some project.” Dean said as he rubbed the back of his neck and looked down at the ground.

“Better say goodnight then, don't want you falling asleep on Sam's paper mache.” Jimmy said with a grin.

Dean leaned towards Castiel who took the hint and met Dean halfway. He kissed Dean slowly, like he was taking his time and Dean let himself relax into it, didn’t push for more, or try to take it deeper. Softly, Castiel’s tongue slipped against Dean’s. His hands found their way to Dean’s hair, and the sensation of his fingernails as they scraped gently over Dean’s scalp sent a little shiver down his spine.

Way too soon, Castiel pulled back with a little lopsided smile on his face and a mix of satisfaction and desire in his eyes. Dean just looked into them for a moment before his eyes flicked over to where Jimmy leaned back against his door.

He gave Dean a look that clearly said _come and get it_ , and like Dean was gonna pass that up. So he walked over and braced one forearm against the door, lifted his other hand to cup the side of Jimmy’s neck and pressed their lips together. Just like Castiel had done for him, Dean took his time with Jimmy; traced his tongue wet and hot over Jimmy’s lips, bottom then top, before he licked into his mouth. Felt so good to have Jimmy pliant against him. If he wasn’t so damn tired, Dean would’ve enjoyed it a hell of a lot more.

“Night, Jimmy.” Dean said softly against his lips as he pulled away.

“Night.” Jimmy replied in an almost dazed sort of voice.

Dean stepped back and Jimmy opened the door, then ducked inside. Castiel went to follow him and Dean couldn’t help but tug him in for another quick kiss because he’d forgotten to tell him goodnight too, “Night, Cas.”

Castiel smirked a little like Dean was being kind of sappy, but he was smiling, so whatever, “Goodnight, Dean.”

Monday rolled around and though Dean seemed happy to see them he was still quiet, just not himself. Jimmy couldn’t stop replaying in his head how awkward dinner on Saturday had been. Even with Dean insisting he’d had a good time it just wasn’t the same as he’d been on their first date. Everything, right down to the goodnight kisses had been more subdued, even the second one he’d seen Dean sneak in with Castiel.

And the texting between them had dwindled. Sure Dean always made sure to wish them goodnight. Sometimes threw in the occasional ‘miss you’. But more often than not he’d take hours to return a text or he’d respond that he was driving and would talk to them later. Seemed like he was _always_ driving.

At the end of the school day, Jimmy was still preoccupied with his thoughts. They were all gathered outside, chatting before they split up for the day. Jimmy was keeping Kevin company while he waited for his bus to pull up. Admittedly, he was doing a poor job of it because he was too busy watching the way Dean shifted anxiously on his feet as he repeatedly looked over at his car while he talked to Castiel.

“Yo, earth to Jimmy.” Kevin’s words finally cut through Jimmy’s thoughts.

“Sorry man, what was that?” Jimmy said.

“I was just telling you how Sam and I almost managed to play through all of Gears of War 4 yesterday. He’s gonna hop on the bus when it gets to the Junior High and come over so we can finish it. My parents think I’m tutoring him for extracurricular credit on my college applications. You know, the ones I won’t be filling out for like another three years.” Kevin finished with an eyeroll.

“Who’re you kidding, they already filled them out for you, they already know exactly what will be on them because they have the next few years planned down to the moment.” Jimmy said with a grin before it slipped from his face. A little lump of dread formed a knot in his stomach,  “Wait, Sam was at your house yesterday?”

“Yeah, all day. Well, not all day. They had their breakfast thing with their dad before Dean brought him over.” Kevin said with a shrug.

“You said Sam’s going over to your place after school?” Jimmy asked.

“Yup, speaking of which, there’s my bus.” Kevin said with a wave before he jogged over to get on.

Jimmy waved back before he turned and headed over to the rest of the group. He spotted Dean as he leaned in to give Castiel a quick peck right before Jimmy reached them.

“Hey Dean, wanna get burgers?” Jimmy asked quickly.

“Oh hey, sorry. Can’t. Gotta grab Sammy and get him home. Some big paper or something.” Dean said distractedly as he turned toward his car. “See you guys tomorrow.” He called as he waved and got into his car.

The knot in Jimmy’s stomach tightened into a heavy stone. First he’d lied about where he was going. Then he’d left without so much as a kiss goodbye. For _him._ Dean’d kissed Castiel; Jimmy could stew on that for days.

Castiel on the other hand, seemed accepting of whatever had Dean acting out of sorts. When Jimmy’d brought it up before, the unflappable Castiel had just shrugged and said Dean would tell them if something was up when he was ready. Problem was that Castiel was too good and selfless. When he cared about someone he always believed in their intentions. He waited patiently.

That just wasn’t Jimmy’s style.

The Impala rumbled to life and started to back out and Jimmy watched it for a second. Then he was on the move.

“Hey Cassie, catch a ride from Balthazar. I’ve got something I gotta do.” Jimmy said as he sprinted toward their car.

He gave Dean just enough time to start heading down the long driveway to the exit of the school grounds and then he followed him, thanked whatever deity was listening that he hadn’t been able to talk Castiel into the bright pink mini custom Cooper and they’d settled on a fairly nondescript black suv. Carefully, Jimmy made sure he hung back just enough not to be spotted while he tailed Dean as he drove through winding neighborhoods.

When Jimmy went to follow Dean around a corner he lost him. There was no one on the road for as far as he could see. Just as he was about ready to turn around, he spotted Dean’s car parked in a large circular drive. For a moment Jimmy assumed it was Dean’s house but then he spotted Dean standing at the door. Quickly, he slammed the car in reverse and backed up ‘til he could just see Dean around the treeline that edged the property. The door opened and Jimmy realized he’d backed up too far to see who answered before Dean ducked into the house.

Irritation and suspicion both fought for dominance as Jimmy pulled up the car up far enough to see the entire entryway and waited. He fielded texts from Castiel, promised to explain where he’d taken off to when he got home, dodged the question when Castiel asked exactly when that would be.

The whole time that he waited, scenario after awful scenario flitted through Jimmy’s head. Sure, there could be a reasonable explanation for Dean’s behavior, but then why would he keep whatever it was a secret and why would he _lie_ to them. Every damn minute that ticked by just made Jimmy that much more sure that something untoward was going on.

Got angrier, and sadder the longer time dragged on. Whatever was going on wasn’t fair to Castiel. Or him, but Jimmy was tough, he could handle disappointment. No one fucked with his brother though.

As it reached the two hour mark, Castiel got more demanding. Jimmy seriously considered giving up and then he saw the front door open again. The brick in his stomach built itself into a three story building as he watched the scene unfold.

Dean sauntered out slowly, clearly worn out and a little sore if how stiffly he was walking was any indication. _What the fuck?_ He was stripped down to just the plain white tee he wore under his uniform, his button up shirt and jacket slung over his shoulder. Odd considering how cold it was. Then Jimmy spotted the woman at the door. She was older but very pretty. And very interested in watching Dean’s ass as he walked away.

It was the content smile that curled up on Dean’s face which Jimmy spotted as he walked around the car toward the driver side that had Jimmy out of his car and storming up the driveway before he had a chance to think about what he was doing.

Hurt and fury flashed hotly through him, and he wanted to stop himself before he made a scene, but he fucking couldn’t.

If he wanted to take Dean by surprise he succeeded. When Dean noticed Jimmy coming up the drive, his smile dissolved and he looked nervously between the front door and Jimmy. Which just added fuel to the inferno of emotion that clawed at Jimmy’s chest.

“Jimmy what-” Dean started, but he didn’t have a chance to finish before Jimmy crowded up in his space, his face livid.

“You know what Dean? I don’t give a _damn_ if you don’t wanna be with me. I get that you just had to put up with me to get to Castiel. But Castiel? He really likes you. And you couldn’t hold out for five goddamn seconds before you had to go looking elsewhere all because Castiel actually wanted to try and make this work as a damned relationship and not someone you just jumped in and out of the sack with?”

“Jimmy!” Dean said, his voice raised as he tried to interrupt him once again.

Jimmy was on a roll though.

“I gotta tell you though, I get why you’ve been so tired. I mean, I’m assuming she didn’t serve you tea first. Two hours, that’s pretty impressive. Granted it doesn’t compare to the day long marathons that Castiel and I have but I guess you aren’t gonna find out how those are since you couldn’t be bothered to keep it in your goddamn pa-”

Dean cut Jimmy off soundly by wrapping his hands around the back of Jimmy’s neck and crushing their lips together. It was rough and aggressive, not dominating like the way Castiel kissed but something different. Something desperate.

Jimmy’s heart pounded loud, blood buzzed in his ears and he was angry, so fucking angry, but Dean just kept kissing him, and Jimmy’s anger dissolved, melted into this kind of achingly sad _hurt_ that stung tears in the corners of his eyes.

When Dean finally released Jimmy and allowed him to take a breath he pressed their foreheads together.

“Why do you _still_ think I don’t want _you?”_ Dean asked, his voice rough and agonized.

“You didn’t kiss me.” Jimmy mumbled as he avoided Dean’s eyes by looking down.

“What?” Dean asked, genuinely confused.

“When you took off. You kissed Castiel goodbye but not me.” Jimmy said, annoyed to feel the prick of tears that built up. “And..” Jimmy took a deep breath and blew it out because this one was something he thought about way too much, “When you kiss us you almost always kiss Cassie first. Like I'm something you forgot… something you _have_ to do.”

“Shit Jimmy, I’m sorry sweetheart. I... I didn’t realize. I’ve just been distracted, tired. That’s just not true though.” Dean said.

Jimmy’s eyes squeezed shut and he bit his lip, hoped the sting would keep tears from falling. Dean was saying he _didn’t_ like Castiel better. And Jimmy desperately wanted to believe he wasn’t just an afterthought for Dean. That Dean liked him too, but even if that was true, he was _still_ lying to them about where he was going.

“What’s going on Dean? You’re lying to us. I know you weren’t with Sam yesterday. Then I find you _here?_ And Saturday… you looked so uncomfortable the whole time Dean, like you didn’t wanna be there. I know you want to be with Castiel so I can only assume it was _my_ company that was objectionable. You _lied_ to get out of spending time with just me. Please, just be honest with me.” Jimmy implored.

“It wasn’t you. It’s just, that kinda place isn’t really where I’m in my element.” Dean said as he shifted uncomfortably.

“Since when is eating not your element, Dean?” Jimmy asked with a smirk that didn’t make it to his eyes.

“Not the food, more the price tag.” Dean said and pulled away, no longer able to meet Jimmy’s eyes.

“Dean… I’m lost.” Jimmy said.

Shakily, Dean sighed a sigh that Jimmy felt to his bones before he looked around and spotted Jimmy’s car on the road.

“Can we come back for your car later? It’s pretty close to your house anyway and I… I gotta show you something before I lose my nerve.” Dean said resigned.

“Yeah but where-” Jimmy started to ask.

“Just get in.” Dean said as he turned and unlocked his car before he slid into the driver seat and stared ahead.

Jimmy did as he was told, waved sheepishly at the woman who still stood at her door while she glared at Jimmy intensely.

The ride was silent and long. Jimmy thought about talking but the resolute set of Dean’s jaw and the way he white knuckled the steering wheel made Jimmy bite his tongue. Even when they left the more affluent neighborhood and drove through town and into the cheaper housing area on the other side. At least once a month Jimmy and Castiel came here because the shelter that they donated to and volunteered at was nearby.

Finally, Dean pulled into the drive of a small, older looking home and cut the engine. Jimmy was confused. His confusion only deepened as they continues to sit there in silence.

“Dean?” Jimmy finally spoke.

“This is where I live, Jimmy.” Dean said while he stared straight ahead at the house.

“What? I don’t-”

“I know it don't look like much, but it’s actually one of the nicer places we’ve lived. For one, it’s a house not an apartment, so, no having to listen to crappy music or loud sex. That last one sounds fun until you realize that it’s some creepy older couple that look like they can’t afford soap.”

“I didn’t realize you were on scholarship but-” Jimmy was interrupted by Dean’s laugh.

It was a twisted laugh that lacked any humor.

“Yeah, no. I won’t be getting any free rides for my smarts. Sammy probably could, but not me. Fact is we’re only there ‘cause Dad got a job working on the buses and that meant free tuition for me and Sam.”

“Dean, that dinner was like three hundred dollars. How did you afford that?” Jimmy asked before it occurred to him that that might not be the best subject right then.

“It’s why I’ve been… weird, I guess. I realized after we went skiing…” Dean trailed off before he took a steadying breath and started again. “I realized how friggin’ outta my league you guys were. I mean, you guys already have each other so even if you _want_ me you don’t really _need_ me. And I got nothin’ to give you in return. I can’t _rent_ out entire mountains. But I can try to at least give you _some_ of what you deserve. So, I picked up whatever work I could get. Turns out rich people don’t like spending money so there are plenty of people willing to hire someone cheap and under the table to do work around their place.”

“So, you’ve been going to school, keeping up with your homework and working every spare moment for peanuts so you could afford an expensive meal.” Jimmy said as things started to click into place.

“Pretty much.” Dean said as shame colored his cheeks.

“And you didn’t kiss me, not because you don’t want me but because you’ve been running yourself ragged trying to… what, make yourself _worthy_ of us?” Jimmy asked while he turned to look at Dean with an unreadable expression.

“Yeah… look I know it doesn’t really compare to what you guys did f-”

Dean hadn’t even heard Jimmy unbuckle but he suddenly found himself with a lapful of very attractive boy intent on covering every last inch of his face with kisses.

“You.”

_Kiss._

“Are.”

_Kiss._

“An.”

_Kiss._

“Idiot.”

Jimmy pulled back to look Dean in the eye for a moment. Then he dipped back in, this time his lips landed on Dean’s. Chaste kisses that rapidly got heated as Dean became acutely aware of Jimmy straddling his lap, knees bookending hips and ass pressed against Dean’s quickly hardening cock.

Evidently Jimmy became aware too because he started to roll his hips just a little. Enough to cause friction. The firm line of Jimmy’s cock pressed against Dean’s belly as he rolled and rubbed against him. Felt so damn good that Dean’s brain short circuited for long minutes.

Suddenly they both pulled away, Dean pressed back into the seat and Jimmy back against the steering wheel.

“Castiel,” They both said in unison.

That was how they found themselves an hour later seated in the twins’ lounge, Dean on the edge of one of the arm chairs and Jimmy only inches away facing him from the low ottoman he’d pulled over to sit on. The two of them practically vibrated as they stared at each other and Castiel paced slowly next to them.

“So, to summarize. Jimmy, you thought Dean’s strange behavior was due to the fact that he didn’t really want you around because he didn’t actually like you but was putting up with you to get to me and then you assumed that he was cheating on us because we, or more specifically _I_ wasn’t putting out. Dean, your strange behavior was a combination of exhaustion from overworking and discomfort over trying to force yourself into a world you don’t actually think you belong in or deserve.” Castiel paused before he turned to face them. “But now you both know that you were being complete idiots and you want to lift the pseudo-ban on sex even though we’ve only had two dates and society would generally feel that for a real relationship that might be moving a little fast.”

Castiel observed the way both of them slumped a little at his words and how their eyes dimmed, but only slightly. He couldn’t keep the small grin off his face as he shrugged.

“Well, we’re three guys, two of whom are brothers, trying to build a relationship. I think we’re pretty screwed by society’s standards as it is.”

Castiel placed a hand to his chin, rubbed at the scruff there. “Now I _could_ just tell you to go ahead and get naked. _Or_ the two of you could show me how good you can be and find just a little more restraint to get you to Saturday so I can plan something a little more memorable than a quick screw.”

Castiel couldn’t be sure if the whimper he heard came from Dean or Jimmy, at this point as tense as they both were in their pure _want_ it could’ve been either. Castiel decided to have some mercy on them. He wasn’t _that_ cruel and the fact that the two of them had managed to talk things out deserved a reward.

“How about a little to hold you over? Why don’t you show me what I missed not being in the car.” Castiel said.

That was all the permission Jimmy needed. He was off his seat and had Dean pressed back into the oversized armchair in a flash, knees spread apart by his hips. Before long they were kissing, hard and fast, as Jimmy rolled against Dean over and over.

Castiel could probably get off on just this. Watching the two of them together, so beautiful as they brought each other pleasure, faces flushed, hair grabbed and tangled beyond saving, marks that bloomed on their skin as they laid claim to each other. Luckily, Castiel had much more control than his brother did and he didn’t plan to come in his pants any time soon.

Dean and Jimmy, on the other hand, looked dangerously close to just such an outcome. But that thought, though satisfying, wasn’t what Castiel wanted right now. It did, however, present an interesting scenario in his head about what kind of situations he might put the two of them in while at school. No, Castiel wanted more. He wanted to see the look on their faces as skin met skin and they painted each other with come.

So, Castiel moved forward and slipped a hand between them, pressed against Jimmy’s chest and separated him from Dean. Both of them looked up at Castiel, and even the haze brought on by lust wasn’t enough to dampen their disappointment. Castiel ignored their looks and reached down to work at Jimmy’s pants with one hand, his other still wrapped around his own waist.

When Jimmy reached down to help, Castiel smacked his hand away before he returned to his task, “Patience, Jimmy. You’ve waited this long.” Castiel murmured as he continued to work.

Finally, Castiel was able to ease Jimmy’s swollen, hard cock carefully out of his pants, made sure the material of his boxers protected him from the bite of his zipper. Clearly Jimmy had been hard for some time, though not nearly as long as the last time Castiel edged him before he’d made him orgasm ‘til he came dry.

Then Castiel was treating Dean to the same. He didn’t have to smack Dean’s hand away, though he did see from the look in Dean’s eyes that it was a conscious effort on his part not to speed things along. An effort that Castiel liked very much.

“Good boy.” Castiel whispered as he pulled Dean’s equally hard cock out.

Castiel lifted his hand up and held it, palm out, in front of Jimmy’s mouth.

“Spit.” Castiel commanded softly.

Jimmy maintained eye contact with Castiel as he leaned forward to start licking at Castiel’s palm. Castiel’s free hand shot out like lightning, fingers wrapped in Jimmy’s long hair before he yanked back hard. Jimmy smirked, but the hunger in his eyes only deepened at the harsh treatment.

“I _said._ Spit. Don’t show off for our guest, Jimmy.” Castiel warned.

 _“Fuck.”_ Dean breathed.

Castiel loosened his grip and Jimmy leaned forward, spit into Castiel’s palm, and did a poor job of hiding his pout. Satisfied, Castiel released him and then moved his slicked up hand over in front of Dean’s mouth.

“Spit, Dean.” Castiel said, his tone a little softer but no less an order.

Dean was in no shape to deny or tease. The exchange he’d just watched had him entirely focused on _not_ blowing his load before Castiel finished with his plans. So Dean leaned forward just a bit and added to Jimmy’s saliva. He expected that was it but then Castiel moved his hand up to his own mouth and, eyes still on Dean, spit in his own hand.

Even though Dean had an idea of what was coming he still couldn’t hold back a hiss when Castiel’s hand lowered and grasped both him and Jimmy together in a tight grip before he pumped them a couple of times, slickly. Then his hand was gone and Jimmy was being pressed back into Dean. This time when they resumed kissing and grinding it was with the added benefit of their cocks sliding hot and hard against each other.

Dean watched Castiel out of half closed eyes as Jimmy sucked and bit along Dean’s jaw. Castiel moved over to the couch before he unzipped his pants and took out his own dick, slowly fisted it as he watched his brother and his boyfriend grind and bite and suck. Even in the low light Dean could see the shiny remainders of their combined spit as it coated Castiel’s cock and it pushed him that much closer to the brink.

“Fuck, Cas, Jimmy.” Dean groaned low.

“The two of you look so good together.” Castiel said, and Dean arched into Jimmy with the praise, loved how it made everything just a little hotter. “I could spend hours watching you just like this.”

Dean’s attention was quickly pulled back to Jimmy when the sharp sting of his teeth just barely missed breaking the skin over his pulse as Jimmy rolled particularly hard against him. The combination of pain and pleasure, all while Castiel watched, with the tension that had been mounting since Jimmy first took Dean in his hand weeks ago proved too much. Burning up with it, Dean came with a guttural shout.

Jimmy’s grin was smug as he pulled back enough to look at Dean’s face. Then his eyes drooped as he bit his bottom lip hard when Dean grabbed his hips and started rutting up into him. Warm come slicked the way even further for Jimmy.

One of Dean’s hands moved up to slide down the back of Jimmy’s open pants, pulled them harder together. Dean’s finger dipped low and pressed firmly against Jimmy’s hole and it was enough to have him bent, face buried in Dean’s neck as he sobbed out his orgasm.

“God, Dean, Cassie, ah, fuck.” Jimmy moaned as he shook against Dean, spilled hot come in between them, added his to Dean’s.

Soothingly, Dean’s hands ran firmly over Jimmy’s back as aftershocks wracked him. So hot that Dean knew he’d be jerking off to this moment for years.

When the waves subsided, Dean had enough thought break through his fog in time to catch it as Castiel pushed his still very hard cock back into his pants before he zipped up.

“Oh, hey. I can… I mean _we_ can-” Dean started.

“I’m good Dean, thank you.” Castiel said with a smile before he stood and walked to the small bathroom.

“But-” Dean tried to protest, he’d never left a partner wanting before and wasn’t too keen to start now.

“Don’t bother.” Jimmy said sleepily, still nuzzled into Dean’s neck. “Also, don’t bother ever trying to edge him. He’s insane and does it to _himself._ ”

“Some people _enjoy_ exercising control over their own bodies, Jimmy.” Castiel said as he came back with a damp hand towel in one hand and a dry one in the other.

“Yeah, and everyone else’s too.” Jimmy muttered.

“I don’t recall you ever complaining before.” Castiel said with a quirked brow.

Jimmy yelped when the wet cloth was dropped without warning onto his head. He pulled the towel off and sat back up, cleaned himself and Dean up as thoroughly as he could, their shirts, though, were a bit of a lost cause.

“Nice aftercare, jerk.” Jimmy grumbled.

“I’m sorry, are you under the impression that anything you just did was trying enough to merit aftercare Jimmy?” Castiel said as he held out the dry towel, swapped with Jimmy and watched as he dried himself.

During their exchange, Dean just sat there and watched. He was starting to get a clearer picture of exactly what he was getting into and while he was a hundred percent on board he definitely was feeling a bit like a fish out of water. Kinkiest he’d ever gotten was when a girl had gotten him to wear her panties but it looked like his vanilla streak might be on it’s last leg.

He could only wonder at what Saturday would hold.


	8. Chapter 8

Okay, so maybe Dean did a lot of wondering. Like _a lot._ And maybe doing a search with the terms edging and aftercare wasn’t the best idea. At least that’s what he realized once the results came back with link after link to BDSM websites. Still, Dean didn’t learn his lesson and soon found himself on a website about kink negotiation and a list of many _many_ different kinks.

At first just reading through the list and thinking about the twins was getting him hard. Thinking of tying one of them up, or even better getting tied up himself painted vivid pictures in his mind. Some of the examples were downright beautiful.

Impact play sounded intimidating until Dean figured out it ran the gamut from spanking ( _hell yes)_ to being punched in the nuts as hard as possible ( _oh fuck no)._ Dean just couldn’t picture either of the twins causing each other _that_ much pain though. But did Dean really have any idea what they got into when they were tucked away in whichever bedroom they happened to pick?

Dean hit the bodily fluids section and stupidly kept reading because he assumed they were just talking about spit and come. But _nope._ Moving on.

When Dean hit bestiality he regretted every single life choice that he’d ever made that led him to that point, quickly closed out the tab and cleared his phone’s history. Then again some of that Japanese porn he liked with the tent-... but nope. _Nope._

Dean had some pretty damn strange dreams that night but by the next morning he was ready to push it aside. Excited to see the twins. No. Excited to see his boyfriends.

He didn’t spot them before class but when Castiel had texted this morning he’d mentioned they were running late so Dean wasn’t surprised. He’d see them in Chemistry. Sure enough when he walked in they were already seated at the lab station. Dean was glad that Josie’s partner was back so he’d been allowed to join Castiel and Jimmy again.

Dean took his seat on the end as usual, though today Jimmy was sitting in the middle when ordinarily it was Castiel who sat there. Usually to keep an eye on wandering hands. Which, hey maybe now that they’d reached the cock on cock stage Jimmy would be allowed and didn’t Dean’s cock just _love_ that possibility.

But Jimmy didn’t make a single attempt to cop a feel. He was off from the start, barely did more than smile and say hello. And he spent the first half of the class squirming in his seat until Castiel snapped at him and told him to control himself. Dean grew more concerned as the minutes passed and Jimmy proved to be more focused on the work than Dean had ever seen him.

When Jimmy came back to sit down at the end of class after cleaning and reshelving their equipment he let out an audible and very pained sounding whimper when he sat. Dean’d had enough.

“What the hell’s wrong Jimmy?” Dean whispered, his voice tinged with a mix of frustration and concern.

Concern that only grew further when Jimmy kept looking down at the table as his cheeks pinked up noticeably. Castiel decided to answer for him when it became apparent Jimmy wouldn’t be.

“Jimmy’s being punished right now, Dean.” Castiel said, his gaze steady and hard as he looked at his brother.

“Punished? How? Why?” Dean managed to ask one word questions.

Castiel leaned in a bit and glanced around to make sure no one else was listening in.

“He has a fairly large plug in right now that we put in this morning. It’s why we were late. He has to wear it the entire school day. Usually I don’t bring this kind of thing to school but as often as I need it, I’m afraid I was stuck for a new punishment.”

“Okay…” Dean trailed off, trying to keep his brain functioning even though the fact that Jimmy was sitting there open and slicked up and ready for Dean to just press… but there was another question that Castiel hadn’t answered. “Why? What’d he do?”

“He told me no.” Castiel said with a shrug as he neatly packed away his notebook and pencils and nudged the still silent Jimmy to do the same.

“Come again?” Dean asked, something cold and a lot like fear twisted in his gut.

“Last night while we were playing after you left, I ordered him to do something and he told me no.” Castiel said as neutrally as if he was discussing their homework assignment. “Oh, it has a remote for the vibrator. Would you like to hold it over lunch, Dean?”

Wide-eyed, Dean looked at the small remote that was held out in front of him in the palm of Castiel’s hand. He looked back at Castiel before he shook his head and mumbled something about not being hungry and getting some air. Dean was on his feet and out of the door, backpack in hand, before either of them had a chance to respond.

He wasn’t fast enough though and he was just turning around the corner of the building to get a moment of privacy in the cool winter air when a hand clasped his shoulder. He didn’t even have to turn around to know that Castiel had followed him.

“Dean, what’s wrong?” Castiel asked, confusion and maybe a little bit of hurt clouded his beautiful eyes.

“I don’t think I can do this Cas. I mean I don’t even know if I coulda really even done the whole two people thing. No idea what the fuck I’m doing, who do I fuck, when, how? But then there’s more. I… there are things… _lots_ of things that I don’t wanna do and…” Dean trailed off as the hurt grew in Castiel’s eyes.

“I don’t… I mean I _do_ understand _some_ of that but I don’t think I-”

“I can’t be okay with being put in situations where I’m punished or whatever because I’m not into something.” Dean said while he looked at the ground.

He hated that he could feel the flush that crept up his face. He felt like a damn virgin who was telling their boyfriend they weren’t ready to have a hand up their sweater.

Then Castiel let out what sounded surprisingly like a sigh of relief.

“Dean look at me please.” Castiel asked, though it was a lot more like a gentle command.

Even after Dean’s little speech that tone still had him complying pretty damn quick.

“You need to understand that there’s a very _very_ big difference between saying no during play and safewording. It’s the whole point of having a safeword. Some people very much enjoy hearing or saying no during play. Jimmy can be particularly petulant. But it’s just another facet. If Jimmy had chosen to safeword there would never have been any punishment.” Castiel cupped Dean’s cheek gently and Dean found himself leaning into the touch. “I would _never_ punish either of you for safewording.”

Dean’s eyes had drifted closed from the touch, which was why Jimmy’s sudden appearance made Dean jump as he spoke.

“Yeah, I was totally being a brat. Earned my punishment.” Jimmy said as he stepped around the corner, almost sounded proud. “I’m just being pissy ‘cause Castiel keeps turning up the damn vibrations only to remind me that I don’t get to come today. _At_ _all.”_

Dean sagged against the cold brick wall.

“I just… I think I might be too damn vanilla for you guys.”

“Dean, what brought this on? You seemed pretty happy with things yesterday. Did I… did I do something wrong?” Castiel asked.

Dean _hated_ that uncertain look on Castiel’s face almost as much as he hated the fact that _he_ was the one that put it there. It was so foreign on him.

“No, yesterday was… amazing. I… I looked up some stuff online last night, some of the stuff you guys said.”

“Oh god.” Jimmy said as he squeezed his eyes shut.

“And what did you find Dean?” Castiel asked, his voice neutral but if Dean didn’t know better he’d swear Castiel was fighting back a laugh.

“Umm… stuff about kink negotiation and a really big list of kinks.” Dean could clearly see that both of them were trying not to laugh now, which only added to the mounting panic that was returning swiftly.

Why weren’t they taking him seriously?

“Cas, I can’t get tied up and smeared with shit.” Dean said, his voice tinged with hysteria.

“Oh _God!_ ” Jimmy exclaimed before he doubled over in silent laughter.

“Dean.” Castiel said, each sound of Dean’s name measured. “I’m going to need to you stop panicking for a few moments so we can have a reasonable discussion.”

Dean was about to argue that he wasn’t being unreasonable but one look from Castiel made him shut up.

“Now, I won’t lie and say that the thought of tying you up doesn’t appeal to me _greatly._ But I can promise you that neither Jimmy or myself have any interest whatsoever in scat play. That aside, I can also promise you that nothing will ever be done to you without your full and enthusiastic consent.”

Some of the tension left Dean but there was still apprehension in his eyes that Castiel noticed. Perhaps they were rushing after all. Perhaps…

“Would you be more comfortable if you established a more physical relationship with just one of us first? You and Jimmy seem to have good chemistry in that regard.” Castiel said, his voice steady and neutral.

“Seriously Cassie?” Jimmy asked, his face lost its previous mirth and his mouth tightened with more repressed words.

“We’ve asked a lot of Dean, it seems unfair that we force him to follow all of our own rules without making any compromises. Especially when we continue our own relationship without him present.” Castiel said as he turned toward Jimmy.

It was Dean, however, who answered.

“No.” Dean said softly.

“Oh, okay. If that… I thought maybe it would help but… it’s a lot. I understand if you’ve changed your mind.” Castiel said; attempted to keep his face schooled but the disappointment and hurt shone through.

“No! That’s not what I… I don’t want just one of you. I just don’t… don’t know if I’d be good enough for _both_ of you… like that.” Dean said, his face once again colored brightly.

“Oh Dean. I doubt a lot of things in this world, but your ability to please us in bed has never been one of them.” Castiel said and reached up to brush a soothing touch across Dean’s cheek.

Dean smiled softly but still Castiel could see doubt.

“I have some thoughts about Saturday. Different than I had been thinking but…” Castiel paused and cupped the back of Dean’s neck gently. “I know we’ve only known each other a short while even though it feels like an eternity. So I know that I’m asking a lot but… can you trust me? Trust that I will never hurt you or push you further than you can handle?”

Dean had no idea why but in that moment, looking into Castiel’s eyes as he waited for a response, Dean’s trust in him was absolute. He licked his lips nervously before he nodded. Wide and happy, Castiel smiled while his eyes tracked the movement of Dean’s tongue before he moved forward and slotted his lips against Dean's and his tongue chased Dean’s back into it’s warm, wet home.

Somewhere in the back of his mind it occurred to Dean that this was the first time Castiel’d initiated a kiss with him entirely on his own with no prompting from Dean. He couldn’t help but wonder if Castiel really thought that Dean favored Jimmy physically, even though it’d been Castiel that Dean’d first met and been interested in.

“We should probably get back in before lunch is over.” Castiel said before he pressed the remote he’d still been holding into Dean’s hand. “Come on.”

He turned and started walking back around to the front entrance and Dean followed quickly behind. Couldn’t resist pressing the button on the small remote though.

“ _Jesus Christ.”_ Jimmy swore loudly from behind them.

The smile that spread across Dean’s face was unstoppable. Maybe this wouldn’t be so bad after all.

***

 **Castiel** **:** _Tying up, is that negotiable? You’d look so pretty bound and waiting for me._

 **Dean:** _Yeah… I think I kinda like that idea._

***

 **Castiel:** _How do you feel about blindfolds?_

 **Jimmy:** _Love ‘em. Unless you’re edging cause you know how I tend to lose control when I can’t see it coming._

 **Castiel:** _…_

 **Castiel:** _I was talking to Dean, Jimmy. I’m very familiar with your lack of control when blindfolded. Also, the fact that you just stopped blowing me to read this and respond earned you ten._

 **Jimmy:** _Hey, you were texting first!_

 **Castiel:** _Yes, but I didn’t have to stop what I was doing in order to do that._

 **Dean:** _Umm… I dunno. Kinda freaked out about the idea of not being able to see something coming to say no if I’m not into it._

 **Castiel:** _Nothing would ever happen to you blindfolded that wasn’t previously agreed upon._

 **Jimmy:** _Oh! How do you feel about rimming?_

 **Castiel:** _That’s five more and if you stop again I’m just going to jerk off and make you watch as I wash all of my come down the drain._

 **Dean:** _Blindfold, okay by me._

 **Dean:** _Rimming’s good too… just never done it, might not be any good at it._

 **Castiel:** _I think Jimmy meant receiving, though I do enjoy the image of your beautiful mouth pressed against his ass. Don’t worry, I’ll be happy to tell you exactly what to do if it comes up._

 **Dean:** _Hey._

 **Dean:** _Is Jimmy still sucking your cock?_

 **Dean:** _‘Cause I’m kinda rock hard right now and wouldn’t mind a picture… if you felt like sending one that is._

When almost ten minutes passed without a response Dean was typing out an apology for overstepping when his phone vibrated in his hand.

 **Castiel:** _I thought this would be more useful than a picture._

Completely floored, Dean watched the seven minute video of Jimmy giving the most leisurely blow job Dean had ever seen. He was close to his own release when Castiel gripped Jimmy’s hair with the hand not holding the phone and yanked him back.

As soon as Castiel’s cock was free, he released Jimmy and gripped himself, pumped once over his spit slick cock, before he painted Jimmy’s content face and open mouth with his release. Then, when he was spent and softening, Castiel released himself and used his fingers to scoop come from Jimmy’s face, fed it into his mouth.

Watching Jimmy suck Castiel’s fingers clean was more than enough to push Dean over the edge and he emptied into his own hand. Just as the video finished another text came in.

 **Castiel:** _Don’t waste it Dean. Clean your hand with your tongue._

 **Castiel:** _And swallow._

Dean could easily say he wasn’t into that. He could just as easily not do it. Castiel wasn’t there and he wouldn’t know if Dean had done as he was told. Still, Dean found that he _wanted_ to do as he was told. Not because Castiel would be happy, but because _he_ would be. So he cleaned up every last drop just as instructed.

 **Jimmy:** _Speaking of clubs, we can go to that club now that we have someone other than each other!_

 **Jimmy:** _Castiel says we weren’t speaking of clubs and if I don’t go to sleep right now he’s going to tie me down, gag me and hide my phone for a week. Goodnight Dean._

***

 **Castiel:** _Public with minimal chance of getting caught?_

 **Dean:** _How minimal?_

 **Castiel:** _Very._

 **Dean:** _Okay, I can handle that._

 **Dean:** _Hey Cas?_

 **Castiel:** _Yes Dean?_

 **Dean:** _Maybe someday I’ll be able to handle a little more than minimal?_

 **Jimmy:** _Sounds good Dean._

***

Saturday found Dean waking up with the sun, a mix of nerves and excitement. The excessively hard morning wood didn’t help. Normally Dean would wake up half mast at most but not this morning. Might have something to do with the fact that he’d gone to bed thinking of finally, _finally,_ getting pounded by two gorgeous guys (or wait, would he be the one doing the pounding?).

Which in turn brought about nerves. Cause sure, he might’ve fingered himself a few times. Heck, one girl he was with, Lisa, almost got her whole hand in once before he had to ask her to let up.

So he might’ve let Castiel and Jimmy believe he’d had a little more experience before but they’d confronted him in the friggin bathroom and had him all screwed up in the head. Couple his lack of experience with his complete lack of knowledge about whatever Castiel was planning and his poor dick was all confused.

Luckily remembering everything he was nervous about the night before was enough to take some of the steel outta his dick so he was able to move about his normal morning activities. He skipped the shower, though, because he wanted to do that right before whatever was happening tonight. He might not know a lot but he knew that clean up _down there_ was a big part of pre-sex activities.

Dean managed to distract himself through the morning by catching up on Doctor Sexy but after he forced down some lunch he found himself reverting to a combination of nerves and guilt.

“Man up Winchester.” Dean mumbled to himself.

Sam, who was still finishing up his lunch at the table, looked up as Dean paced the kitchen.

“What’s eatin’ you?” he asked.

“Nothin.” Dean growled.

“Got a hot date with your boyfriends?” Sam asked with a grin.

Dean stopped to glare at Sam.

“Oh my god. Are you guys gonna _do it_ tonight?” Sam practically squealed with delight.

“Shut it, Sammy.” Dean warned.

“Like, how does that work exactly? I mean I know like how it is with two guys but… what about three? Is it like a train? Or… holy crap do you put two dicks in the same place? Oh! Dean, are you gonna take it or give it?”

“Keep it up, bitch. I’ll be sure to get to your school early enough to ‘run into’ that little blonde chick I know you’ve been hanging out with. I’ve got a few naked baby pictures that’ll just _have_ to end up in my wallet before then.”

“Okay! I’m sorry! I’ll stop!” Sam threw his hands in the air in surrender.

Dean decided to ignore the mumbled ‘jerk’. He had something more important to do and if he didn’t do it now then he might not ever. And he was coming to the realization that this might be important.

 **Dean:** _I’m a virgin._

 **Castiel:** _What?_

 **Jimmy:** _Come again?_

 **Dean:** _Not a Virgin, virgin…_

 **Dean:** _I’ve never had sex with a guy._

 **Jimmy:** _Holy shit. I did Not see that coming._

 **Dean:** _Cas?_

 **Dean:** _Cas, seriously. You there?_

 **Castiel:** _Sorry, had to take Jimmy’s phone away. He was… less than enthusiastic about the idea so I had to cuff him to the bed until I was finished or he learned how to not be an insensitive twit._

 **Dean:** _So… basically until you decide you're done._

 **Castiel:** _Likely._

 **Dean:** _So._

 **Castiel:** _Thank you for sharing that Dean. I’m sure it wasn’t easy. I wish you’d felt more comfortable with sharing it earlier but I understand._

 **Castiel:** _Would you like to postpone tonight? We won’t be upset if you aren’t ready._

 **Dean:** _No! I’ve never been more ready for something in my life._

 **Dean:** _Just not really sure what exactly it is I’m ready for…_

 **Castiel:** _I promise I’ll take care of you._

Something warm built up inside Dean when he read Castiel’s last text. It was a concept that seemed so foreign to him. Being taken care of. It’d been a long time since his dad had made the internal decision that not only could Dean survive without his constant attention, he could take care of Sammy too.

Dean didn’t blame his dad either. He really had done the best he could. But with no real family to speak of and the job market being shit when his mom died he was suddenly a single parent with only one income. Luckily government funding helped out enough for Sammy to be taken care of during the day while he was too young for school but as soon as he hit kindergarten that funding had disappeared. And that just left Dean. So someone else taking care of him was just a distant memory and the idea that Castiel was going to do that for him… that pesky warm, tender feeling swelled in his chest again.

Still, Dean was full of nervous energy and couldn’t stop pacing.

“Fuck.” Dean muttered. “Sammy! Let’s go down to the park and shoot some hoops!”

When Sam and Dean got back to the house he had about an hour to get ready before the boys would be picking him up. They’d promised they were gonna take their own car, which Dean was really grateful for. Getting picked up by a limo would likely bring up some uncomfortable questions with his dad. He of course knew the kinds of people Dean was friends with but still, friends didn’t usually pick up friends just to hang out in a limo. That definitely implied date.

As Dean washed off the grime and sweat he’d built up kicking Sam’s ass at basketball he couldn’t help but let his thoughts wander. And the places they wandered to had him trailing a hand down his soaped up stomach to tease at his quickly hardening cock. It took a lot of restraint not to jerk off, just to take the edge off.

But something told him Castiel would be less than thrilled if he knew Dean had taken care of himself before their date. Not that he wouldn’t be able to get it up again. One of the perks of only being a few years off from puberty was the remarkably short refractory period.

Instead Dean did a very, _very_ thorough cleaning of his undercarriage then twisted the knob and doused himself in a quick cold rinse which did the job of managing his body so he’d be able to dress without discomfort. And that brought on a whole new set of issues. Castiel had insisted he didn’t need to dress up, that the date before the main event was going to be totally casual but _their_ version of casual and _his_ tended to be light years apart.

 _It wasn’t this hard getting ready for my date with Bela,_ Dean thought. Then again his date with Bela happened before he truly had a sense of what kind of life these people really lived. In the end Dean settled on a newer pair of jeans that were only a little worn at the knees and a soft forest green henley that he knew brought out the color of his eyes.

Dean’d just finished tying his boots when he heard a car pull into the driveway. He grabbed his jacket and threw it on before he stuffed his phone and wallet into his pocket. He was almost out his bedroom door when he remembered the stapled packet of papers that’d been sitting on his desk for the past few days ever since he’d liberated them from Dad’s desk. He rolled them up and jammed them into his back pocket before he left again.

Speak of the devil, when Dean came tearing around the corner into the living room Dad was just heading to the door to answer the knock.

“Hey Dean, where-”

“Going out with some friends, might be late, might crash at their place. Be back for breakfast. Bye!” Dean said as he rushed to the door.

Quickly yanked it open and almost barrelled right into Jimmy and Castiel.

“Let’s go.” Dean said as he moved toward the car.

He had to come to a fairly abrupt stop when he got there, unsure where to go. They’d never used the twins’ car before. Unlike the Impala the front only had two seats. Which meant Dean had no idea where he was supposed to sit.

“You can have shotgun.” Jimmy said as he came up behind Dean, leaned a little closer to him than Dean was comfortable with right then.

So he stepped away from Jimmy and glanced nervously toward the house before he headed to the passenger side and slipped in. Jimmy and Castiel exchanged looks before they walked toward the car and got in. When Jimmy slid into the seat behind Dean he leaned forward and hooked his chin on Dean’s shoulder.

“You’re not out to your dad yet, are you?” Jimmy said.

Dean had expected the question but not the understanding and warmth Jimmy’s tone took on.

“No.” Dean said as he studied his hands and his voice dropped down to a near whisper. “I’m sorry about that.”

“Hey.” Castiel said, then reached to wrap his fingers over the top of Dean’s hands. “It’s okay. Now we know. Not like we have any room to judge.”

“Right, we better get going, it’s almost a two hour drive.” Jimmy said as he sat back.

When Dean pulled his belt across and pressed the buckle into the clip he felt the brush of papers sticking out from his back pocket.

“Oh, hey.” He said as he pulled them out to hand to Castiel. “I brought these for you.”

Castiel took them and unrolled the papers, smoothed out the wrinkles before he looked up at Dean with a questioning raise of his eyebrow.

“You brought me the results of your physical?”

“I had to get one done when I transfered so I got the whole gamut… third page.” Dean said as he shifted uncomfortably and tried to hide the flush that rose on his cheeks by looking away.

He heard Castiel flipping through the papers before there was a sharp intake of breath.

“I… I haven’t been with anyone else since then and… well since you and Jimmy have only ever been with each other, I figure that means you're clean too. Just so you know… for later… if you want.”

“Dean.” Castiel’s voice was low and almost dangerous. “If it weren’t for the fact that your father could look out any moment, I’d have you bent over in the back seat. The fact that you’re going to let me feel you, skin to skin, that I get to watch as Jimmy swallows your come for me is nearly enough to make me lose control. Nearly.”

Dean swallowed hard as Castiel turned the key in the ignition and backed out of the driveway. It was gonna be a long two hours.

Of course, Jimmy’s motivation for giving up the front seat became crystal clear about a half hour into the drive. The time had passed quickly when Dean broke into a tangent about how classic rock was far superior to any of the crap produced today after Jimmy’d made the mistake of admitting he didn’t really care for Led Zeppelin.

Eventually, Dean fell quiet with one last mumbled retort about Jimmy’s bad taste and he slumped back into his seat with a scowl. The click and soft snick of a belt retracting was all the warning Dean had before there was a hand sliding between the seat and the door and along Dean’s hip. Warm breath ghosted over Dean’s ear as Jimmy pressed against the back of the seat to speak.

“Let me make it up to you.” He said hotly before his hand found it’s mark and squeezed Dean’s cock gently.

The soft moan that escaped Dean was irrepressible as all the previous tension from his shower came roaring back.

“Oh fuck.” Dean whimpered as Jimmy massaged the growing bulge in his pants.

Briefly, Castiel spared a glance from the road, looked over and smiled at his boyfriends before he returned to his vigilance. He did manage to catch Jimmy’s other hand as it slipped around the other side of Dean’s seat and reached for Dean’s nipple. The startled gasp that came from Dean let Castiel know Jimmy’d found what he was looking for.

Without a doubt, Castiel enjoyed the noises that came from Dean as Jimmy jacked him to hardness and beyond through his pants. As Dean’s breaths came quicker and became more ragged Castiel stole another quick look. Dean’s head was tipped back and toward his window which allowed Jimmy room to work at Dean’s neck with his tongue and teeth. Jimmy’s hand was working at a near frenzied pace on Dean’s cock. He’d also abandoned Dean’s nipple to rub at his own hardon.

“Jimmy stop.” Castiel ordered, his voice left no room for argument.

Castiel was pleased to see that Jimmy responded instantly and pulled back. Dean whimpered as Castiel went back to watching the road again.

“Sorry, Dean. Wouldn’t want you to make a mess in your pants before we get to our destination. After… well I think by then you’ll be able to hold out for me like a good boy, won’t you?” Castiel said softly as he reached out to run his fingers over the abused skin of Dean’s neck.

The shiver he felt at his fingertips that emanated from Dean had the semi that Castiel was sporting fully hard. He ignored it and returned his focus to driving. The rest of the trip was spent talking about school and arguing over the radio. Dean pitched a fit when Britney Spears came on but Jimmy noted with a smirk that he was quiet as a church mouse when it was Taylor Swift.

Finally, Castiel turned off the road and parked the car. Dean was confused. He wasn’t sure what he’d been expecting but with a two hour drive it definitely wasn’t some small town diner with a dirt parking lot.

“Bathroom break?” Dean asked.

“Nope.” Jimmy said as he got out of the car and stretched. “Final destination.”

Castiel got out as well and headed toward the door without a word. Dean got out and scrambled after them. It was a fairly average looking diner, nothing stood out much from the many others he’d been to before. Dean’s confusion only grew when they walked through the door.

“Castiel! Jimmy! What’re you guys doing here? You’re a little early for your trip, ain’tcha?” An older woman who stood behind the long counter called out.

“About nine months, Dorothy. We missed you too much to wait though.” Jimmy said before he winked at the woman.

Dean stood there a moment and then he let Castiel usher him to a corner booth with a half circle bench. Obediently, Dean slid in, followed by Castiel. Jimmy slid in on the other side of the booth and they moved in until Dean was bookended by the twins.

“This is our very favorite place to eat Dean.” Jimmy said as he handed him plastic sheathed menu.

Dean noticed that neither twin cracked open theirs.

“Really?” Dean asked as he looked over the menu, though he clearly had trouble believing it.

“Really.” Castiel said with a grin. “If it wasn’t so far away we’d probably be here every weekend.”

“So how exactly did you end up here?” Dean asked curiously, somewhat distracted by the array of his favorite food listed on the page.

Before they had a chance to answer two glasses were placed in front of the twins, a chocolate milkshake for Castiel and a strawberry milkshake for Jimmy.

“How bout you, hon? Can I get you a drink?” Dorothy asked with a warm smile.

“Umm, vanilla shake?” Dean asked wide-eyed.

Next to Dean, Jimmy snorted and Dean felt Castiel’s foot bypass his own right before Jimmy hissed in pain.

“Comin’ right up sugar.” Dorothy said with a wink before she turned on her heel.

“She knows your drinks without you ordering them?” Dean asked somewhat incredulously.

“She knows our entire order without us ordering them.” Castiel said.

“So… how’d you guys find this place?” Dean asked again.

“Well our parents were dragging us to some insanely boring New Years party with some of Father’s business partners. Which sucked ‘cause Cassie promised me he was gonna fuck me for the first time that night. I mean, we’d done plenty of hand jobs and blow jobs and he’d fingered me-”

“Stay on topic please, Jimmy. Dean really doesn’t need to know about our sexual awakening.” Castiel sternly said.

“Well… maybe another time?” Dean asked hopefully.

“I’ll tell you later.” Jimmy stage whispered to Dean.

“Anyway, as Jimmy was saying, we were on our way when the limo broke down. We still had another hour and a half to our destination. Unfortunately what with it being New Year’s Eve, the local mechanic was unavailable. The company we contract our drivers through would have been able to get a new car out to us but the closest one not in use was two hours away. Father even tried to find someone around that would sell their own vehicle but nothing.” Jimmy stopped when Dorothy came back with Dean’s shake.

“What can I get you sweetie?” Dorothy asked.

Dean noticed she didn’t carry a pad or anything.

“Umm, I’ll have the bacon cheeseburger, loaded with the ketchup on the side and fries, extra crispy if you can please?” Dean said before he handed the menu back to Dorothy.

“Ain’t that the cutest thing ever!” Dorothy exclaimed before she headed back into the kitchen.

“Umm… what is?” Dean asked looking back and forth from Castiel to Jimmy.

Castiel had a small smile on his lips as he was suddenly fascinated by the chipped surface of the table but it was Jimmy that answered.

“That’s Castiel’s order. Exactly. Right down to the crispy fries.” Jimmy said with a grin.

“Oh.” Dean said softly, cheeks flushed with just a hint pink.

“So anyway, we broke down just up the road a bit so instead of waiting in the cold car we walked back here. They were actually just getting ready to close down for the day but when they heard what had happened and how long we were going to be waiting for they kept the kitchen open. By the time the new car got there, Dorothy and her husband had already called their family to come down and celebrate New Year’s here and the party was in full swing. They didn’t even think twice about just… claiming us as family.” Jimmy stopped to sip from his shake, a sight that Dean thoroughly enjoyed.

“Between the kindness they treated us with and the fact that the food was better than any Michelin Star restaurant, it easily became our favorite place. Now every year our family makes the trip out, the day before New Year's Eve so that Dorothy’s family can enjoy the holiday.” Castiel said.

“So if you come here for New Year’s with your family, why are we here now? Not that I’m complaining. Gotta say diner food probably only comes in third after sex and my Baby. But…” Dean trailed off, not really sure where to go.

“We’ve probably spent several hundred thousand dollars in one year alone satisfying our every whim. But our very favorite place is here. We don’t _need_ expensive dates and gifts.” Castiel said as he reached over to grasp Dean’s hand. “We just. Need. _You.”_

Jimmy wrapped his fingers around Dean’s other hand where it was resting under the table on Dean’s thigh. For a few moments he basked in the warmth and caring he felt practically radiating off the twins. The spell was broken though when Dorothy arrived with their orders. She set two identical looking baskets in front of Dean and Castiel and a plate with chicken fried steak, mashed potatoes and green beans, all drenched in white gravy in front of Jimmy.

Dean watched as Jimmy dragged a finger through the gravy before he sucked it between his lips and moaned obscenely. He opened his eyes and caught Dean staring. With a grin Jimmy dipped his finger back into the gravy and held it up to Dean’s lips.

“Try it, second best white stuff I like to swallow.” Jimmy said with a smirk.

Nervously, Dean looked around the diner and saw that the few customers that had a view of their booth were wrapped up in their own meal and Dorothy had disappeared into the kitchen. He dipped down and wrapped his lips around Jimmy’s finger, sucked hard and twirled his tongue around the tip for far longer than was actually necessary. Finally, Dean straightened and let Jimmy’s finger slip from between his lips. He couldn’t help but grin at Castiel’s smirk and Jimmy’s rather dazed expression.

“You’re right, it’s pretty damn tasty.” Dean said as he picked up a fry and dragged it through Jimmy’s mashed potatoes and gravy before he popped it into his mouth.

Castiel chuckled as Jimmy frowned and pulled his plate closer, guarding it from further pilfering as he ate. The three of them tucked into their food relatively silent in appreciation of the mouthwatering tastes.

So wrapped up in eating the best damn burger he’d ever had, Dean didn’t even notice Jimmy moving until he felt fingers pull at the button of his jeans. He nearly choked on his mouthful when his zipper was tugged down and warm fingers snaked through the opening of his boxers to wrap around his cock.

Wildly, Dean looked around. Of course Dorothy chose that moment to start walking toward their table. Fast as he could while acting naturally, Dean slid forward in his seat to make absolutely sure that everything was hidden by the table as Jimmy started to slowly fist his rapidly filling cock.

“How’s everything boys?” Dorothy asked cheerfully.

“Perfect as always, Dorothy.” Castiel said before he took another bite of his burger.

“Still best I’ve ever had.” Jimmy said with a grin as he sipped from his straw.

Dorothy looked over at Dean with an expectant smile and Dean stared back as he forced down his bite of food. When Jimmy squeezed Dean’s cock he really did choke on the food that was sliding down his throat. He scrambled for his shake and took a sip before he managed to speak.

“Everything’s great, Ma’am. Never had a better burger.” Dean barely said without a stutter.

Dorothy nodded and gave Dean strange look before she went back to the counter. If Dean thought that Jimmy would stop now that their audience had left he was sadly mistaken. At a leisurely pace, Jimmy resumed jacking Dean as he alternated eating with his left hand and sipping his shake.

Just as Dean was beginning to tense up, his orgasm nearly cresting, Castiel firmly said, “Enough Jimmy.”

Softly, Dean whimpered a little at the denied release when Jimmy took his hand off his cock but he was grateful he wouldn’t be walking out come all over his shirt and pants. He took a few steadying breaths and then reached down to tuck himself back in. A bit of a struggle now that he was rock hard and he couldn’t contain a hiss that escaped when the cold metal teeth of his zipper brushed against his heated flesh. Jimmy smirked as Dean adjusted and left his pants undone until he softened.

Which wasn’t gonna happen any time soon. He’d just started to lose some of the steel while he finished his burger when a hand from his right slipped up his lap and reached into his boxer shorts. Dean’s eyes flashed up to look at Castiel, who was casually working on his french fries as he occasionally dipped one into his shake before he ate it.

Once again Dean found himself trying to school his face as he choked down food and got jacked nearly to completion. This time he absolutely whined when he was denied his release. He was _so close_ when Castiel roughly pushed Dean’s cock back into his boxers and began to polish off the last of his shake.

After that, Dean started to eat quickly, hoped to finish before another round of whatever the _fuck_ was happening. Didn’t even stop when he got a brain freeze from downing his shake too fast. He grabbed a napkin and wiped his lips off before he tossed it onto his empty plate triumphantly.

His triumph was short lived.

“Jimmy why don’t you show Dean where the bathrooms are. It’s a long ride back. I’ll order dessert while you’re gone.” Castiel said and Dean caught his smirk before Jimmy pulled him out of the booth.

Dean had just enough wherewithal to zip up his pants so they at least looked secure, narrowly missed catching his still semi-hard cock in the teeth. He staggered after Jimmy toward a small hallway that led parallel to the kitchen. Then Jimmy pushed through the door marked Men and dragged Dean in behind him. As soon as they cleared the door Jimmy spun around and threw the lock.

“Jimmy what-” was all Dean got out before Jimmy dropped down to his knees in front of him. “Oh, fuck.”

His fingers swiftly had Dean’s zipper fully unzipped, and his boxers pushed down. Without so much as a single word, Jimmy fisted his hand around the base of Dean’s cock and closed his lips over the head. Flicked his tongue around the sensitive underside of it a few times, and then swirled his tongue, dragged the tip along Dean’s slit, before he sucked him down until his lips met his fist.

So fucking hot, felt so good that Dean had to bite his bottom lip to keep from moaning. One of his hands ended up in Jimmy’s hair, the other ran down the side of Jimmy’s neck, over his shoulder and back again repeatedly while Jimmy sucked his cock, and his hand slick with spit kept time with his mouth.

Tight, wet, hot, Dean was close in very, very little time. Didn’t help the way that Jimmy’s lust-bright eyes stayed locked on Dean’s, so sexy with his cheeks flushed dark pink, looking every bit as turned on as Dean was.

“Fuck, Jimmy.” Dean groaned quietly, his body tense, so, so, so close.  He closed his eyes, his head tipped back and he concentrated on the heat that built up inside him, the pleasure that washed through him. 

Just as his muscles locked up, Jimmy abruptly stopped. Pulled off and let go of Dean’s cock, his chest heaved and he looked like it was every bit as hard for him to hold back as it was for Dean.

Suddenly, exactly what Jimmy and Castiel were doing became crystal clear; they were edging him. Everything in Dean was screaming at him to just wrap his fingers around his cock, just a few quick jerks and he’d come. He panted with the effort of restraining himself, his fingers twitched at his sides where he forced them to stay.

So hard it fucking _hurt,_ but he didn’t wanna disappoint Castiel, and Jimmy was staring at him with wide hungry eyes, and he’d been so good for Castiel, Dean could too.

“Deep breaths.” Jimmy finally said, still slumped on the floor, back against the door. “It helps.”

Dean nodded and made himself take some long breaths until he’d calmed enough to gingerly tuck himself back into his boxers, and pull the same half-zipped up thing he’d done before with his pants.

With a warm smile, Dean helped Jimmy to his feet, then pressed him back up against the door, kissed him hard and deep and punishing. Rocked against him, dragged their hard cocks together through way too many layers in a rough grind, slow hard circles. Perfect fucking friction, basically torture for Dean, but he smirked when he pulled away because Jimmy looked so damn good like that, eyes glassy with desire.

“Can’t let you have all the fun.” Dean said as he flicked the lock open, and tugged Jimmy forward a few steps so they could open the door.

Jimmy’s lips parted like he was gonna say something but nothing came out, so Dean took him by the hand and brought him back to their table, flashed a grin at Castiel when they slid into the booth and Castiel glanced between them with a raised eyebrow and an amused hum.

While they’d been gone apparently Castiel had ordered pie, which woulda been great if Dean wasn’t so hard. Kinda difficult to enjoy the perfect apple pie in front of him when the only thing he could think about was all the ways Jimmy and Castiel could get him off.

Miraculously, Dean made it through desert without any more incidents. He figured they’d decided to take it easy on him, at least until the car. Fuck, there was still the whole drive home to get through. Two hours with Jimmy behind him? Hot as the idea was, Dean didn’t know if he could handle that.

So after they’d paid and said their goodbyes, Dean had insisted that he’d take the backseat. This time Jimmy was driving but he didn’t think for a second that Castiel being the one in back was gonna be any kind of reprieve. Thankfully, Castiel just smiled and told him it was fine if he took the back.

An hour, that’s how long Dean’s breather lasted. There was a click of a seat belt buckle releasing and then Castiel climbed into the backseat with him. Dean’s eyebrows raised, but Castiel didn’t move a muscle toward him. He just twisted enough in his seat to face Dean and slowly undid his own pants. Even in the dark of the car, Dean could make out enough of what Castiel was doing to see when he pulled his cock out, eyes on Dean’s the whole time.

Slowly, Castiel started to jerk himself off, heat pooled in Dean’s groin. So fucking hot, just watching Castiel fist himself in long perfect strokes. Castiel’s head leaned back against the window, his eyes half-closed but still focused on Dean.

“Fuck, Cassie.” Jimmy whined from the front seat and Dean’s eyes met Jimmy’s for a moment in the rearview mirror before Jimmy’s flashed back to the road.

Castiel’s teeth dragged over his bottom lip and Dean wanted desperately to cross the space between them, kiss him hard. Harsh breaths and the slick sound of Castiel’s hand on his cock filled the car, Dean reached for his belt but Castiel shook his head just a little. Frustrated, Dean let out a little groan and adjusted his aching cock before he settled back, resigned to watching without being allowed to touch.

Sexy little grunts and groans broke free from Castiel’s chest as his hand sped up and Dean got the feeling he really, really liked being watched. Dean’s extremely hard dick made sure he knew damn well how much _he_ liked to watch, too.

A quick rub of his palm over the head of his cock and a stuttered gasp, then Castiel gave Dean a little smirk and tucked himself back into his pants. Dean let out a breath he hadn’t noticed he’d held. So turned on that thinking straight was much harder than it oughta be.

“So what did you think of the diner, Dean?” Castiel asked conversationally, like he hadn’t just jacked himself off nearly to orgasm.

Dean’s brain blanked for a moment before it cleared and he managed a strangled, “It, uh, was great. Shake was awesome.”

Jimmy chuckled from the front and Dean rolled his eyes, a grin on his face. Normal conversation resumed after that, and the next half-hour went by pretty quickly. Dean’s dick didn’t fully soften, but it was a lot easier to ignore it when he paid attention to Jimmy and Castiel as they talked. That worked right up until Jimmy told a story about the time he tried to convince Castiel to try out for cheerleading because Jimmy wanted to do it but he wouldn’t without Castiel.

“You should’ve seen him.” Jimmy said with a laugh, “He looked ridiculous trying to act all peppy when we practiced at home. The look on his face was so painful to watch that I had to give in and take mercy on him.”

On the outside Dean laughed. On the inside he was busy picturing Jimmy in a cheerleading skirt. Which was pretty fucking hot, and Dean was all kinds of screwed. His cock jerked in his pants, and he bit his lip to hold back a groan.

Like he’d noticed Dean’s reaction, which knowing Castiel he had; Castiel unbuckled his seatbelt again, got Dean’s undone, then pinned him up against the door and kissed him just the way Dean’d been fantasizing about. Used his thumb to pull Dean’s bottom lip down and slid his tongue hotly into Dean’s mouth. Sucked Dean’s tongue into his mouth and scraped his teeth gently over it while his hands effortlessly freed Dean’s cock from his boxers again.

Dean had just enough time for a quick exhale before Castiel expertly sucked his cock. Easily settled into a rhythm that made Dean’s head fall heavily back against the window and a low groan spill from his lips.

“Jesus, Cas.” Dean breathed, hands already in Castiel’s hair as pleasure built up rapidly in his gut. “Please, fuck, _please.”_

“Fuck, you sound good when you beg.” Jimmy muttered from the front, voice strained.

Castiel pulled off long enough to say, “Focus on driving, Jimmy. Hands on the wheel.”

God, Jimmy whined like he was the one who’d been brought to the edge nearly half a dozen times instead of Dean. Wasn’t time to dwell on that though, because Castiel licked a slow trail around the head of his cock, laved over the slit just before he swallowed him down again. And _fuck,_ slick hot suction engulfed Dean’s cock. Felt so good. Close, Dean was so- so- so _fucking_ close, “Please, please, Cas, please. Fuck, oh my God, _please.”_

“Fuck, Cassie.” Jimmy groaned sympathetically, “He sounds so wrecked.”

One last long, ridiculously slow suck up Dean’s length and Castiel popped off with an obscene wet sound that sent another surge of heat to Dean’s cock. And, fuck, the whimper Dean let out was embarrassing as fuck but he wanted to come so _goddamn_ badly.

“Cas- I can’t-” Dean gasped uncontrollably, “I can’t.”

Careful not to touch Dean’s cock, Castiel leaned over Dean and caught his lips in a deep kiss. Frantically, Dean clung to him, kissed him back with all the desperation he felt.

“Shh.” Castiel murmured against his lips, “Yes, you can. You can do this.”

“Deep breaths,” Dean replied nonsensically, his lips brushed Castiel’s with each word, eyes closed tight.

“Exactly.” Jimmy said calmly, “Deep breaths.”

Castiel’s hands ran soothingly through Dean’s hair as he softly kissed him until Dean once again calmed down enough to tuck himself back into his pants. Even the subtle friction from his boxer-briefs was almost too much, but Castiel’s thumb as it brushed softly over Dean’s cheekbone was grounding, kept him subdued.

“Good, Dean, you’re doing so good.” Castiel said softly, “We’re almost home. When we get there, Jimmy and I will take care of you, okay?”

Dean nodded as his breathing slowed back to normal, “Yeah, okay.”

“I promise this will be worth it. You have no idea how hot it is to see you fall apart like that.” Castiel said and Dean couldn’t hold back a little moan at his words. “This is what I want to do: I’m going to tie your hands to my bed posts and blindfold you. We thought that might take some of the pressure off of being with two people. Does that sound alright to you?”

While he considered it, Dean chewed lightly on his bottom lip, then said, “Okay. Um, just so… Just so you know, I uh, I’m okay with bo- with whatever. I mean, you know I haven’t, but I-I definitely _want_ to.”

“That’s good. We only want to do this if _you_ want to. Which is why we need a safeword from you. Realistically we probably should’ve had one before we started edging you, but that part wasn’t _entirely_ planned.” Castiel admitted with a smirk.

Nervousness exploded in Dean’s stomach, but he pushed it down because he trusted Castiel. Trusted Jimmy.

“Okay, ummm. I dunno… Never had to pick one before.” Dean mused as he struggled to come up with something that didn’t sound utterly stupid, “Impala work?”

Castiel’s lips turned up in a wide smile, “Hear that Jimmy? You owe me a hundred dollars.”

Dean raised his eyebrow when Jimmy cursed.

“I said you’d pick that. Jimmy thought you’d pick Chevy.” 

Dean’s eyes flicked to Jimmy’s in the mirror, “Really? Chevy?”

Jimmy pouted just a little, “Oh c’mon, like that’s any worse than Impala.”

“Oh yeah?” Dean asked with a smirk, “What’s yours?”

Almost on cue, Jimmy’s cheeks flushed dark pink and he avoided looking back at Dean as he pulled into the driveway for their house.

“Jimmy.” Castiel said with clear amusement, “Tell him or I’ll make it extra embarrassing.”

Jimmy scoffed and mumbled, “Chicken Little.”

Dean laughed, “I’m sorry, did you just say your safeword is _Chicken Little?”_

“It was Jimmy’s favorite story when we were children. Our nanny used to read it often. Apparently it stuck with him and much, much later when we found out about proper BDSM practices, safewording and such, Jimmy’s first thought was Chicken Little.” Castiel said with a way too amused smile.

“And you mocked Impala.” Dean said with a smirk.

“Yeah, yeah. We’re here.” Jimmy grumbled as he parked the car.

Dean’s nerves flared up again as they slipped quietly into the house, and made their way to Jimmy and Castiel’s wing. But Castiel’s hand firmly in his, and Jimmy tucked up against his side, under his arm, kept Dean from worrying too much.

Calmly, Castiel led them to his room, which was dimly lit with recessed lighting over the head of his king size four poster bed. A plush pale grey bedspread lay perfectly tucked in and way too many dark grey pillows of various size lined the top. If it weren’t for a few band posters on the back of Castiel’s door, the room would definitely look like something out of a magazine. Pristine and tidy, well decorated, and Dean had to wonder if Castiel had picked any of it out at all.

After he’d given Dean a few moments to take in his surroundings, Castiel pulled him closer, pressed his body right up against Dean’s and kissed him deeply. Trailed his tongue over Dean’s bottom lip before he sucked it into his mouth and bit down gently. Dean groaned and rocked into him and then Castiel pulled back, guided Jimmy in to kiss Dean.

Jimmy’s lips were hot against his, and Dean slid his hands down to Jimmy’s ass, tugged him into a slow grind that burned pleasure through him. Had to break the kiss when Castiel peeled Dean’s shirt off over his head, and Jimmy took the opportunity to get his off too, before he crashed back into Dean passionately.

“Jimmy, get his pants off.” Castiel said, so controlled, and Dean’s dick ached at the low, rough tone of it.

Jimmy nodded, then pressed wet, hot, open-mouthed kisses along Dean’s neck as he scrambled to get his jeans undone. Popped the button, got the zipper down then dropped to his knees and pulled Dean’s jeans down. Helped him out of his shoes, and socks, and then steadied him while he stepped out of his pants.

There was something utterly vulnerable and so fucking hot about standing there in his underwear while Castiel was fully dressed and Jimmy was still in his jeans. Before Dean could think about it too much, Castiel’s lips were against his ear and he whispered, “Go lie back on the bed Dean, hands above your head.”

Dean bit his bottom lip but did as he was told, climbed onto the bed, and positioned himself just like Castiel had said. Turned on so much more than he’d ever been before as Jimmy and Castiel both stared at him for a moment, cheeks flushed, eyes dark. Their breaths came just as fast as Dean’s.

“Blindfold.” Castiel said to Jimmy, and Dean just barely picked up on the strain in his voice, but it was there and fuck it was hot to hear him like that.

“Yes, Sir.” Jimmy instantly replied, went into Castiel’s nightstand and came back a moment later with a silky black blindfold, handed it to Castiel without prompting.

Warmly, Castiel smiled at Dean as he walked over to the bed and crawled up beside him. Jimmy followed suit on Dean’s other side, and Dean nervously licked his lips. Then the blindfold was pulled over his eyes and Dean sucked in a slow breath.

“Still okay?” Castiel asked, and Dean nodded. “I need you to use your words today, Dean. Yes or no?”

“Yes. Yeah. I’m good.” Dean answered.

Not being able to see them was a shame, because they looked so fucking hot right then, but when they started to trail hot kisses along either side of his neck, his jaw, Dean found himself paying much more attention to the sensations that rushed through him in response. Felt amazing.

A hand skimmed up each of his arms to his wrists, and then cool, smooth leather cuffs were buckled around them. As the hands smoothed over his wrists and fingers slipped between the leather and his skin to check the fit a brief panic caused Dean to tense up.

“Dean?” Castiel asked softly.

“Yeah, I’m good. Just, new, ya know?” Dean said breathily.

He made himself relax, which wasn’t all that hard when Castiel whispered, _good,_ into the skin of his throat before he kissed his way down to lick and suck at Dean’s nipple. Jimmy did the same on the other side, and fuck that felt so fucking good.

Little groans and moans fell helplessly from Dean’s lips. Already on edge after all the teasing he’d been through. Dean’s hips involuntarily pushed up off the bed, and firm hands closed over them, pushed them back down hard.

“Fuck.” Dean breathed.

After that Dean lost track of who was where as Jimmy and Castiel shifted around each other, tasted and felt every inch of his body, and Dean figured that was the purpose anyway, so he stopped trying to figure it out when someone peeled his boxer briefs off and lips closed so hot around his cock.

Hands drew his legs up by the backs of his knees. Spread them wide, and left him totally exposed. Fucking hot. Sweat beaded on Dean’s skin and anticipation mixed with the pleasure that already coursed through his body.

Slick and gentle, a tongue slid slowly from behind his balls, down over his perineum and back further. Dean’s breath caught in his throat as it circled his asshole. Little shocks of pleasure and embarrassment lit him up, brought a darker flush to his skin. God, that felt so damn good. So different, but _God,_ good.

At first it was just little kitten licks over and around his rim, but as he relaxed into it, they became longer, firmer until gradually it started to push inside him. Hot whimpers and ragged breaths exploded from Dean’s lungs. Sensations so far removed from anything he’d ever felt, but he quickly found he loved it.

“God, Jimmy, Cas, fuck.” Dean moaned as the tongue pushed in deeper still, the mouth on his cock sucked hard and slow up to the head of his cock and then popped off.

A little strangled whine left Dean’s throat at the loss, and then he echoed it when the tongue in his ass retreated as well.

“Please, please, fuck.” Dean said, voice nearly unrecognizable, “Jimmy, Cas, I need you.”

“Shhh.” Castiel soothed him, “Dean, I know you want to come, but we’re going to take this slow. Make it good for you. You want that, right?”

Dean’s breath caught in his throat but he managed to stutter out, “Y-yeah.”

“Just trust us.” Jimmy said before a soft warm kiss was placed on Dean’s lips, “We’re gonna blow your mind, Dean.”

“Too late.” Dean said grumpily, “It’s already blown.”

Two warm chuckles echoed in the room, and Dean smirked. Quickly forgot why he was smirking when a slick wet sound filled the air. The sound of fingers sinking into a body. Dean desperately wished he could see whose fingers were sliding into whom, and the little whimper he made let them know it too.

A few torturous moments went by with nothing to concentrate on but those sounds and his own curiosity about what was gonna happen next. His dick was so fucking hard and he was so ready for this. Whatever the hell _this_ ended up being.

And then knees settled on either side of Dean’s hips and, _“Oh, fuck.”_

A little hot pressure against the head of Dean’s cock and then he slid slickly inside of someone. Tight, unbelievably tight, and hot. Dean couldn’t get over how hot it felt. How tightly it gripped him. Slowly sank around him until he bottomed out, ass flush with Dean’s body.

“Holy fuck.” Dean whispered before slick lips pressed against his in a deep kiss as the body on top of his bent forward to kiss him.

Probably in an attempt to distract him while slick fingers massaged around his hole. Dean felt something soft nudge at his hip. He took the hint and lifted his hips, whoever was on top of him moved with him, and a pillow was slid beneath his ass. Then, just a bit of warning before one of the fingers that’d been circling his rim slid slowly inside. Different than the tongue, harder, but it felt just as good. A little weird, kinda burned a bit, but so good.

Dean groaned out his pleasure into the mouth that was hot on his. Wanted to touch them so badly, but his hands were cuffed to the bed posts, and _fuck,_ it was so damn hot. Another finger slipped inside of him and Dean arched into it, stung a little, but that just added to it, made it hotter, and Dean fucking loved it.

The fingers crooked just right and, _“Oh my fucking god.”_

He didn’t have to see to know that matching smug grins were aimed at him right then, but he didn’t care because, _“Do that again._ Please?”

Wordlessly, Dean’s request was granted, and he bucked up involuntarily into the body above him. Startled a little groan out of him, not much but enough that recognition lit up in his brain like euphoria, “Jimmy.”

“How did you-” Jimmy started to ask, but Dean cut him off with a loud moan as another finger pushed gently inside of him, stretched him with a burn that Dean was quickly getting addicted to.

Dean couldn’t help the way his hips flexed, pushed back onto Castiel’s fingers and up into the tight, wet, heat of Jimmy’s ass. Instinct and pleasure drove him, and his body chased sensation. Like it couldn’t decide which it wanted more, and then Castiel’s fingers slowly withdrew.

Another slick wet sound, and then Castiel quietly said, “Dean, what I want is to fuck you while Jimmy rides you. Is that okay?”

“Fuck, yes.” Dean groaned, his chest heaved with heavy breaths.

Pressure, so much pressure against his hole, slick and hot and his body resisted. Dean bit his lip and forced himself to relax, to _trust_ Castiel. And then Jimmy’s tongue slipped into Dean’s mouth, brushed against his and Dean focused on that, on the way Jimmy kissed him like he wanted to devour him.

Finally, Dean’s body gave and Castiel pushed in achingly slow in a series of shallow thrusts that grew deeper until he was fully inside of Dean. The breath he’d been holding left Dean’s lungs in a rush, right into Jimmy’s mouth.

“You’re doing so good.” Jimmy said softly against his lips, “You feel so good.”

“So do you.” Dean panted, felt so full, and stretched.

Different, odd, but fucking _awesome._ And Jesus, he’d just popped two metaphorical cherries at the same time. All Dean really wanted now was to fucking come, every single cell in his body ached with the need, and he writhed restlessly between Jimmy and Castiel.

“I take it you’re ready?” Castiel said like his dick wasn’t buried inside of Dean, how the fuck did he do that?

Dean’s own voice was breathy and strained when he replied, “Fuck, yes. Just please, fuck me. Both of you.”

Like Dean’d flipped a switch their movements were instantaneous and in sync. Castiel withdrew almost all the way and Jimmy lifted up off Dean. Then they slammed into and down on him, and Dean cried out. Couldn’t help any of the sounds he made after that, couldn’t muffle them if he tried.

Hard and fast, Jimmy dropped down on his cock over and over. Castiel was more gentle, but just as exacting. Each perfectly timed thrust brushed against Dean’s prostate with clinical precision. Cracked pulses of electric pleasure through him and tightened the coil of heat in Dean’s gut.

With how worked up he’d been it wasn’t long before Dean was on the knife’s edge of coming. So damn close, “I can’t, Cas, Jimmy! I’m gonna, fuck, sorry. Wanted, _ah, fuck.”_

“Just let go, Dean.” Castiel said, “Jimmy, tell Dean how badly you want him to fill you up.”

Dean groaned, felt his balls draw up tight as Jimmy panted, “God, Dean, want you to come in me so badly. Please, please, Dean. Wanna feel your hot come inside me.”

“Yeah, fuck.” Dean panted as his body stiffened just before his hips jerked in a wash of pleasure so intense it was almost painful as he came in hard pulses, way more powerfully than he was used to. “Jimmy, Cas, fuuuuck.”

Intense gratification thrummed through Dean as his climax slowly subsided, didn’t know if the violence of his orgasm was due to the edging or just to Jimmy and Castiel, but fuck if he really cared right then.

A moment later, Jimmy slid off him and Dean already missed the warmth. Castiel withdrew a second later and Dean’s blindfold was pushed up. Dean blinked as his eyes adjusted to the light, took a moment for them to focus. Jimmy and Castiel were kneeling on either side of his shoulders while their hands furiously pumped along their lengths.

“How would you feel about us coming on your face?” Castiel asked, Jimmy just groaned as his eyes flashed from Dean’s face to Castiel’s hand on his own cock.

“Yes.” Dean answered quickly, “Yeah, fuck, want you to do that.”

Castiel nodded and Jimmy bit his lower lip. Their cheeks were flushed bright pink, vibrant blue eyes locked on Dean as they jerked off over him.

“Fuck, you’re gorgeous.” Jimmy said breathlessly. “So goddamn hot.”

Dean’s cheeks flushed and his spent dick gave an interested little twitch.

“He’s right,” Castiel agreed, “You’re perfect. So good for us.”

“Can you…” Dean said, “Can you kiss each other while you finish?”

A patently dirty grin crossed Jimmy’s face and then Castiel used his free hand to pull Jimmy into a heated kiss, so sexy that Dean was already half-hard again. Castiel bit down on Jimmy’s bottom lip hard and Jimmy came with a drawn out groan. Warm come splattered across Dean’s face and he gasped in a turned-on breath.

A couple moments later Castiel’s lips parted, his body froze, and he came silently. Added his come to Jimmy’s, so fucking hot. Dean’s cock was fully hard again, already aching for touch. There was something irresistibly hot about Castiel and Jimmy marking him up like that.

Both of their eyes traveled from Dean’s face, down over his body and Jimmy’s lips curved into a smirk when they caught on Dean’s swollen dick.

“Looks like someone’s ready for round two.” Jimmy said airily.

“Can’t help it. You’re both hot as fuckin’ hell.” Dean said with a cocky smile.

Castiel looked at Dean consideringly for a moment, and then seemed to make up his mind, “Jimmy, lick Dean’s face and neck clean.”

Slow pleasure lazily suffused Dean as Jimmy followed Castiel’s instructions to the letter. At the same time, Castiel’s hand closed tightly around Dean’s cock and jacked him off in a leisurely rhythm that made Dean’s toes curl.

Dean’s orgasm built up in gradual degrees as Jimmy finished with his face and moved on to the hollow of his throat. Sucked and licked there while Castiel sped up his pace. Finally crested when Castiel bent forward and caught his lips in a possessive kiss that burned through him.

Heat burst in Dean’s chest and flowed out through his body as he came, rolling waves of pleasure fluctuated in little peaks until they faded into a warm satisfaction that left him boneless.

His mind floated, semi-conscious for a while and when he came back to himself, his wrists had been uncuffed, Jimmy was tucked along one side of him, Castiel on the other, and the blanket had been pulled up. He could feel where Castiel was smiling against his neck and Jimmy pressed a kiss to his chest.

“Hope someone cleaned us up before you pulled the blankets up.” Dean said thickly, still half out of it.

“Like Cassie would ever let us sleep like that.” Jimmy said with an eyeroll.

“So,” Castiel said, a slight nervousness in his voice, “What did you think of that?”

Dean reflected for a moment and tried to come up with the right words, settled on, “It was fuckin’ awesome. Wanna do it again soon.” Dean shifted a little at the slightly uncomfortable feeling in his ass, “Well, not too soon. Pretty sure my ass is gonna need some recovery time.”

Warm laughter rang out and Jimmy and Castiel settled happily back down against him. Dean’s lips curved up in a smile, content. For all his nervousness, this’d been one hell of a night.

“Hey, Cas?” Dean asked hesitantly, face flushed.

“Yes, Dean?” Castiel rumbled as his fingers trailed gently along Dean’s ribs beneath the warm blanket.

“Maybe… maybe next time you could… you could come… inside me? Not that I didn’t love that.” Dean said in a rush. “But I kinda wanna… want you to…”

Dean couldn’t quite finish.

“Why, Dean.” Castiel said darkly. “I do believe you have a claiming kink.”

Dean felt his cheeks grow impossibly warmer as he stayed silent.

“Dean, I would love nothing more than to mark you, inside and out.”

With that, Dean let his eyes drift closed, reveled in the press of warm flesh all around him. Eventually Castiel made them get up for a midnight snack and some juice. Gave Dean a pair of pajama bottoms that fit mysteriously well before they headed down to the kitchen. Dean just accepted them with a soft smile and then after they’d eaten they brushed their teeth, and climbed back into Castiel’s bed.

He fell asleep in between two of the most gorgeous boys he’d ever known, and thanked his lucky stars that they’d met. No place else he’d rather be right then.

After that night, Dean had kinda expected that once that dam broke that it would be all sex all the time. But aside from a couple of stolen moments at school and spending the night with the twins that Saturday which ended up being fairly standard… as standard as sex with three guys got, anyway… their time was spent mostly just being together, doing stupid stuff like playing video games and watching crappy tv. Hanging out like they had before and Dean had to admit, he really fuckin’ liked it that way.


	9. Chapter 9

Human Biology was usually a pretty interesting class. Dean didn’t mind it at least, and he didn’t have any issues with the teacher, so that was a plus in his book. He sat tucked away in his now standard seat toward the back and jotted down pointless notes that he wouldn’t really need for studying; just gave him something to do with his hands instead of fidgeting.

This morning when he’d gotten to school Jimmy had seemed a little off, but he’d smiled all warm with just a hint of want when he’d said he was fine. Dean was working on his trust issues, so he let it go. Couldn’t help thinking about it now though.

In his pocket, Dean’s phone buzzed. His stomach sort of lurched because he’d set it to silent, and only specific contacts would alert. Those being Dad, Sam, Castiel and Jimmy. He worked his phone subtly out of his pocket and held it under his desk while he hit the power button. The screen lit up and Dean licked his lips at the cryptic text.

 **Castiel:** _Tell your teacher you’re feeling unwell and come to the boys locker room._

The phone vibrated again in his hand.

 **Castiel:** _Now, in case that was unclear._

 **Dean:** _Uh, what’s up Cas?_

 **Castiel:** _Dean, now._

Dean’s stomach fluttered. No idea what this was about but he had a bad feeling it had something to do with why Jimmy had seemed a little shifty earlier.

 **Dean:** _Yeah, ok._

Dean packed away his stuff and made his way up to the teacher. Told her he felt sick and then left when she excused him. From there, he made his way down to the gym, which was empty save for Castiel who stood in front of the locker room. _Where was Jimmy?_

As Dean got closer, Castiel opened the locker room door and then guided him in before he locked it behind them. Then Castiel walked around Dean until he stood in front of him, filling out his school uniform in a way that Dean would probably never be used to.

“What, um, what’s goin’ on, Cas?” Dean asked a little weakly.

Castiel’s lips pursed for a second like he was confused and then his face cleared up with a little smile, “Oh, you thought something was wrong. No, Dean, Jimmy and I wanted to do something to mark the anniversary of our first month together.”

Woah. Wait. What? Was Dean supposed to have gotten them something? Shit. Was he supposed to have anticipated this? They’d only been together for a month and apparently Dean was already fucking it up royally.

“Stop panicking.” Castiel said fondly, “We _wanted_ to surprise you. You’ve been _such_ a good boy for me Dean. So good to Jimmy and me, that we wanted to do something for you. Something we both noticed you took an interest in when it was brought up.”

“Oh.” Dean said, kinda puzzled and still a little guilty.

Castiel just smiled though, and then said, “Happy anniversary Dean.”

His words must’ve been Jimmy’s cue, because right on schedule he walked out from behind a row of lockers and Dean’s lips parted in a mix of shock and arousal. Jimmy stopped next to Castiel, and Dean took a damn good look at him dressed in a girls school uniform; Black Mary Janes, grey knee high socks, smooth perfectly tanned thighs that gave way to a grey plaid skirt, white button up shirt complete with blue tie and a navy blazer. And he looked fucking hot as hell in it.

“Jesus, Jimmy.” Dean breathed when his eyes finally made it up to Jimmy’s.

 _Fuck,_ Jimmy’s cheeks flushed a little, so pretty and sexy, that Dean’s cock rapidly hardened just watching him. Castiel quirked a proud sort of smile while he moved behind Jimmy, tucked his chin over Jimmy’s shoulder and smoothed his hands over the flat surface of Jimmy’s belly.

“Mmm. He looks so perfect like this doesn’t he?” Slowly, Castiel’s hands skimmed down Jimmy’s skirt, the whole time his eyes stayed locked on Dean’s, even when Jimmy’s head tilted back and his eyes closed. “That’s just the beginning though. Let’s-” Castiel’s fingers caught the hem of Jimmy’s skirt, “Show him what’s underneath, shall we?”

A shudder wracked Jimmy’s body as Castiel slowly dragged his skirt up, inch by inch until he revealed hot pink lace panties that just barely contained Jimmy’s hard cock.

“Fuck.” Dean whispered, so turned on that he ached with it; wanted to drop to his knees right there and run his tongue over Jimmy’s length, taste him through the delicate material. “Can, uh, can I-”

“This is all for you, Dean.” Castiel replied. “Do anything you want, except get Jimmy off. He’s not allowed to come today. Isn’t that right, Jimmy?”

Jimmy’s breathing hitched before he sighed, “Yeah.”

Castiel’s hands stilled just framing Jimmy’s cock where it strained his panties, so close to where Dean knew he was desperate for touch, “What was that?”

“I-yes, Sir.” Jimmy stuttered.

And _fuck,_ didn’t that send a little shiver down Dean’s spine; pushed him to action too. He walked the few steps between him and Jimmy then kissed him, hard and fast, like he couldn’t fucking wait to taste him. Brutally plunged his tongue into Jimmy’s mouth on a groan with none of the usual teasing brushes of lips that were unique to them.

Damn if Jimmy didn’t love it though, because he arched into Dean, rubbed himself shamelessly against Dean’s dick, and moaned into Dean’s mouth. Needy, and desperate and so goddamn hot that for a minute Dean just let himself enjoy it.

Right up until Castiel’s voice brought Dean back to himself, “God, you two are so hot.”

“Why?” Dean asked curiously. “I mean, why isn’t he allowed to come?”

“Because _Jimmy_ needs to learn to control himself. He spent all week texting with you about panties and nearly ruined the surprise.” Castiel said.

“I was excited.” Jimmy pouted and Dean soothingly ran his tongue over Jimmy’s lips before he moved to treat Castiel to the same.

Hot in his ear, Jimmy’s breaths came in pants, and Dean knew he wanted to watch, but trapped between them he was too close to get anything close to a good view. Had to settle for listening to the wet sound of them kissing.

Absently, Jimmy’s hips jerked forward then back, like he couldn’t decide if he wanted to grind his cock against Dean’s or his ass against Castiel’s dick. So sexy, and Dean sucked on Castiel’s bottom lip for a moment, then raked his teeth over it.

“Hmm. Let’s get this jacket off him first. Then I wanna taste him.” Dean said low; his breath hot puffs against Jimmy’s ear that caused him to shiver against them.

“Just a little.” Castiel warned lightly as he helped Dean slide Jimmy’s blazer off his shoulders and let it fall to the floor, “Jimmy’s been excited all morning and while I would love to see just how messy he can get these panties before we’re through with him, he knows he’s got to be a good boy for us.”

Dean leaned back, his dark eyes caught Jimmy’s and Jimmy bit his lip, blushed all over again, and just looked so innocently shy. Which Dean knew from experience, he absolutely wasn’t but _fuck,_ did he ever play the part well.

“That true Jimmy? Is that why you were so weird this morning?” Dean asked softly.

Beautifully, Jimmy’s blush spread to the tips of his ears and he shook his head. Castiel’s hand slipped into Jimmy’s hair and he tugged his head back, his lips brushed Jimmy’s ear while he said, “Your words, Jimmy, use them. Answer Dean just the way you’d answer me. This _is_ supposed to be for him after all.”

“Yes, Sir.” Jimmy replied instantly, eyes unfocused and lust-glazed.

Well, fuck, was Dean _ever_ gonna get used to how damn hot that was? His cock already throbbed in his pants and he palmed himself for a little relief before he resumed his line of questioning.

“So if that wasn’t it, what was going on?” Dean asked as his eyes flicked between Castiel and Jimmy.

“Why don’t I show you?” Castiel proposed and Jimmy sucked in a sharp breath.

Dean nodded his agreement, and Castiel turned Jimmy in his arms until Jimmy faced him, then he pulled up Jimmy’s skirt again, this time without the tease. Made Jimmy tilt his hips so his ass stuck out and then tugged the panties to the side so that Dean could see the wide base of the pink silicone plug he had in.

“Fuck,” Dean said, “That’s so fucking hot.”

“Isn’t it?” Castiel asked conversationally, like he hadn’t just moved his thumb to press against the base. Like Jimmy hadn’t just shuddered against him with a little pleasured whine. Like Dean didn’t almost come in his fucking pants just from watching it happen. “It’s rather large too. Much bigger than anything Jimmy’s used to wearing in public, but we’ve been practicing for this.”

Dean’s eyebrow lifted curiously, “This?”

“Would you like to tell him, Jimmy?” Castiel asked, finally addressing him.

Jimmy buried his face in Castiel’s neck, but he spoke clear enough for Dean to hear him, “Want- I want you…” Castiel’s fingers gave the plug a little twist and Jimmy groaned, “And-and Cassie to, fuck, ah, to fuck me at-” Castiel tugged the plug a bit, “Mmm… at the same time.”

“Holy shit. Really?” Dean couldn’t hide the excitement in his voice because he’d be lying if he said he hadn’t jerked off to that thought a time or several. “Can you even…?”

Castiel smiled proudly at Dean, “Like I said, we’ve been practicing. Jimmy’s able to take me and a pretty sizeable toy at the same time. The research I did showed that it’s actually easier with two-”

“Cas, I’m gonna cut you off there.” Dean said with a smirk, “I’m _way_ more interested in testing out your research than talkin’ about it.”

“Me too.” Jimmy mumbled into Castiel’s neck, “Sir.”

Briefly, Castiel narrowed his eyes at Dean before he too admitted, “Yeah, okay.”

“So how do we…” Dean said, then paused to wet his lips before he continued, “How is this gonna work?”

Castiel smiled a soft little smile at him, and Dean’s heart jumped in his chest, “All you need to do is lie back on that bench. Jimmy and I will take care of the details. We’ve been-”

“Practicing, yeah, got that. So, you wanna do this right now? Or you think we should tease him a ‘lil more first?”

A distressed little whine came from Jimmy, and Castiel rubbed his back soothingly, “I think what Jimmy means to say is that he’d prefer it if we fucked him instead of making him wait, but as it’s your gift, it’s up to you.”

“Look at me, Jimmy.” Dean ordered, and Jimmy instantly looked over his shoulder to meet Dean’s eyes.

There was desire, desperation and longing all plain to see in his gaze, and Dean knew that despite the fact that Jimmy absolutely _could_ take more teasing, he was already on edge. Didn’t wanna get him too worked up, too out of control, not yet anyway, so he just said, “Okay.”

Dean stepped forward and pressed a soft kiss to Jimmy’s lips and tugged off his own blazer, let it fall to the floor with Jimmy’s. Pulled his tie loose and dropped it too. Then he slowly unbuttoned his shirt while matching sets of blue eyes hungrily watched his deft fingers undo each button until his torso was bare, and his shirt hung open.

Next went Dean’s shoes and socks followed by his belt, pants and boxer briefs until he stood there in nothing but his open shirt. Felt too exposed to be fully naked in the locker room, but Jimmy and Castiel didn’t seem to mind.

Already hard and leaking, their eyes were both focused on where Dean’s cock jutted heavily out, nearly hard enough to press up against his own belly.

“See something you want?” Dean asked cockily, he wasn’t expecting Jimmy’s breathy _yes_ to follow but it did and his dick bobbed in response. “Let’s do something about that then.”

Castiel nodded, eyes dark, and he pulled Dean into a harsh kiss before he told him to lie down on the bench. Dean complied easily, laid flat on his back, legs bent at the knees and spread wide, feet firmly planted on the floor. He watched while Castiel helped Jimmy out of his panties and shoved them into his pocket before he slowly withdrew the plug from Jimmy’s ass. Eyes closed, Jimmy’s cheeks were stained dark, his lips swollen and shiny when he bit down on his lower one to muffle a moan that tried to escape.

“Holy fuck.” Dean gasped, honestly a little shocked, “No fucking wonder you were shifty this mornin’.”

“We weren’t sure how much time we’d have to get him ready once we got you here.” Castiel informed him as he brought Jimmy over to straddle Dean’s lap.

Jimmy’s legs ended up on either side of Dean’s thighs, feet stretched to the floor. He bent forward and placed his hands on Dean’s shoulders, Dean’s own moved restlessly over Jimmy’s back as he shifted to catch Jimmy’s lips in a deep kiss right before Castiel’s hands skimmed up the back of Jimmy’s thighs, and rucked his skirt up around his waist.

There was a click of a lube cap, and Dean braced himself just as Castiel’s fingers closed wet and hot over his hard cock, gave it a couple of jerks and then held him still for Jimmy. “And Jimmy didn’t want to wait even if we _did_ have unlimited time.”

“Yeah, yeah, we get it: I’m impatient.” Jimmy grumbled. “Can you just both fuck me already?”

The crack of Castiel’s other hand as it landed on Jimmy’s asscheek echoed in the locker room, so fucking hot, almost as sexy as the gasp Jimmy let out and the way he rocked back into it like he wanted more. He shot a glare over his shoulder at Castiel, who just smirked with one eyebrow raised like he was daring Jimmy to complain again.

Fortunately, Jimmy didn’t. He just rolled his eyes and then faced Dean again. Slid his tongue into Dean’s mouth as he sank down hot and wet around his cock with nearly zero resistance. Dean’s hips flexed but he held himself still, let Jimmy maintain control. So goddamn hot the way Jimmy bounced in his lap a few times like he couldn’t help himself. Like he wanted to get Dean in as deep as he could.

And then Castiel’s finger pressed in alongside Dean’s cock in an easy slide and Jimmy threw his head back on a ragged moan. _Fuck,_ Dean didn’t have words for how fucking good it felt. Pleasure buzzed under his skin in steady waves, and that was _before_ Castiel got a second finger in. Before he got three in. Jimmy took it like a fuckin’ pro, covered in a sheen of sweat, little desperate tears in the corners of his eyes as he begged Castiel to just fuck him, _please, Sir._

Looked so fucking pretty in his skirt, sweat dampened shirt and tie. Dean could see the outline of his hard cock where it pushed up the front of his skirt, reached between them to pull the material up and out of the way so he could see the swollen-hard shiny cock it hid. _Jesus._ So fucking hot.

“God, Jimmy. So fucking g- _God.”_  Dean took a shuddering breath and then looked past Jimmy, got caught in Castiel’s stare. “Cas… If-ah- If we’re gonna do this, it needs to, fuck, needs to happen now.” Dean groaned as Jimmy rocked down hard on his cock, on Castiel’s fingers, “I don’t- I can’t-”

“Okay, Dean.”

Castiel’s fingers slipped free with a wet sound that Dean _felt._ So damn hot and then even hotter because Castiel undid his pants, shoved them and his underwear down just enough to free his hard, thick, cock. Slicked it up and then pressed it insistently against Dean’s, and with just the tiniest bit of resistance Jimmy’s body gave.

Pressure so exquisite that Dean lost his breath wracked him as Castiel’s cock pushed in beside his and Jimmy, _fuck,_ the moan he let out was hot and so loud that Castiel’s hand clapped over his mouth to silence him. Draped over Jimmy’s back, Castiel sucked a kiss into the juncture of Jimmy’s neck and shoulder. So goddamn hot, Jimmy’s eyes were desperately locked on Dean’s while his chest heaved and needy little muffled noises leaked out around Castiel’s fingers.

“Shhh.” Castiel soothed him, and Dean echoed it, ran his hands down Jimmy’s sides until he settled them on his thighs.

Then Castiel reached into the pocket of his pants, which were barely hanging onto his thighs, and pulled out Jimmy’s underwear. Stuffed them into Jimmy’s mouth and Dean had to close his eyes and breathe for a second because it was too fucking hot watching Jimmy’s lips close around the pink lace. He fucking bet Jimmy could taste his own precome on them, and that thought alone almost made Dean come right there.

And then Castiel started to rock his hips. The slick drag of Castiel’s cock against his inside of Jimmy snapped Dean’s eyes open and he looked up into the perfect blue eyes of _his_ twins, both so intensely focused on _him,_ and warmth swelled in Dean’s chest, this big, huge, _feeling_ for them that nearly overwhelmed the pleasure which steadily coursed through his body.

“Cas, Jimmy.” Dean groaned, voice thick and like they just understood Jimmy fell forward and tucked his face into the crook of Dean’s neck and Castiel sped up his thrusts.    

Fuck, Jimmy was so tight around them, so hot and slick that Dean couldn’t help but roll his hips up, instinctively tried to push in deeper and Jimmy panted sweltering breaths against Dean’s sweat-slick skin. Strangled moans bounced off the walls, echoed around them and Dean couldn’t even tell who was making them. Just felt too goddamn good to care.

“Fuck,” Dean groaned low when Jimmy tensed up a little, the pressure around their cocks so good it almost fucking hurt. “God, Jimmy, you’re so tight.”

“He’s right.” Castiel agreed, way less affected than he should be, Dean thought, “You feel amazing.”

Jimmy just held on tighter to Dean, made these little whimpers in the back of his throat that pushed Dean high, fast. Concentrated heat built up low in Dean’s gut, so fucking close.

“I’m gonna- I-I-” Dean panted, and one of Castiel’s hands slid down to twine with his on Jimmy’s hip. The tangled mess of warm feeling in Dean’s chest coalesced with the heat in his groin, swelled up until it felt like it’d swallow him whole. “I can’t, I’m gonna- fuck.”

Castiel’s lips twitched up into a little smirk, “Who says we don’t want you to? I, for one, definitely want to know what it feels like when you come inside Jimmy, hot against my cock. Want to feel how much slicker he’ll get, how much hotter.”

 _Fuck, fuck, fucking, fuck,_ Dean pushed in deep and came in hard pulses, spilled inside Jimmy, all over Castiel’s cock with little jerks of his hips. Beyond fucking hot, Dean groaned when Castiel slammed harder into Jimmy while aftershocks still shook him. And Jimmy moaned through it all with needy cries of pleasure.

Before Dean’s cock even had time to soften, Castiel came too, and the warm come that flooded Jimmy in gushes nearly had Dean fully hard again. So _hot._ After Castiel finished, he carefully pulled out and Dean’s cock slipped out along with him.

The little whine Jimmy let out at the loss cut off abruptly, and Dean looked down to see- _holy fucking Christ,_ Castiel’s entire fucking hand as it disappeared inside Jimmy at the same time as Castiel’s other hand wrapped around Jimmy’s cock and stripped it roughly. With the way Jimmy rocked back onto Castiel’s fist, Dean made an educated guess that Castiel was using his _fucking fist_ to massage Jimmy’s prostate.  

Didn’t take long at all for Jimmy’s body to lock up in ecstasy, not when Castiel was so clearly using every trick he knew to get Jimmy off fast. Frantic frenzied moans filtered loudly through the soaked panties in Jimmy’s mouth right up until Jimmy’s breathing froze and his muscles tensed while he tried to fight it.

And then all of a sudden Jimmy’s hips jerked wildly and he painted Dean’s chest with streaks of warm come as he gasped for air. _So fucking hot, God._ Took a couple moments after that for Jimmy to actually come down, and when he did he pulled his panties out of his mouth, glared over his shoulder at Castiel.

“No fair, asshole. You did that on purpose.” Jimmy complained.

“Did what?” Castiel asked, not entirely pulling off the innocent act.

“You said I couldn’t come and then made it impossible not to.” Jimmy said with a pout.

Castiel looked way too smug as he slowly withdrew his hand, Jimmy didn’t even wince, “I know.”

Jimmy’s glare narrowed further, “So you can’t punish me for that.”

“Can’t I?” Castiel teased as he wiped his hand off on Jimmy’s skirt.

“Eww, gross, and no! It’s not fair. You knew I was gonna come and you kept going.” Jimmy said sulkily.

“He’s kinda right, Cas.” Dean said, then held up his hands when Castiel looked at him one eyebrow raised, “Just sayin’.”

Castiel shrugged with a grin then moved to help Jimmy off of Dean. After that they stripped down and took quick showers in separate stalls. Which Castiel insisted upon _again_ but this time because they probably didn’t have much longer before the bribe they’d given the gym teacher wore off and he came back to check on things.

Once they were all dressed, Castiel checked his phone and decided they had time for a few more lazy kisses up against the lockers before they made their way to Chemistry. Each brush of the twin’s lips stoked the warmth in Dean’s chest, until Castiel finally dragged them off to class with one last whispered _happy anniversary._


	10. Chapter 10

“Hey Dean. Umm… there’s something I should probably-” Jimmy started as he stood with the front door barely cracked open while Dean stood on the front steps with his duffle in hand.

Suddenly the door swung open and the way Jimmy’s body wrenched with it, clearly he’d been attempting to hold it closed.

“Well _hello!_ Who’s this then?” Someone Dean didn’t recognize asked as he jostled Jimmy out of the way.

Dean wasn’t proud of the twinge of jealousy he felt when he looked at the guy who was standing closer to Jimmy than was polite for friends. He looked like he was couple of years older than Jimmy, even though Jimmy had a few inches on him. Shaggy sandy brown hair and bright hazel green eyes that radiated warmth. Objectively he was pretty cute, but Dean wasn’t about to admit that.

Neither Castiel nor Jimmy mentioned having company when they’d invited him to spend Spring Break with them.

“You’re early Dean!” Jimmy said with a smile that looked a little too forced.

“I guess I was a little anxious to get here so I could kick your ass again on that pool rematch you insisted on.” Dean said as he shifted awkwardly.

Never occurred to Dean that they might not _want_ him to come over early… ‘til now.

“Nonsense. Gabe Adler does _not_ spend a Saturday sitting at home like a spinster. Especially when _that_ is just sitting there begging to be ridden. Sweet ride!” Gabe said as he brushed past them and headed for Dean’s car. “Jimmy get my coat and your boy. We’re going _out._ C’mon Dean-o!”

“That’sourcousinGabedon’tleavehimalonenearyourcar.” Jimmy spit out as he grabbed Dean’s bag and turned on his heel.

That was all the warning Dean needed and he jogged after Gabe. When he got to the car Gabe was already standing at the passenger door. Dean felt a small twinge of annoyance. Jimmy and Castiel always sat up front with Dean when they took his car.

“Well, let’s go! I’m freezing my piece off over here and it’s far too magnificent to lose.” Gabe said and waggled his brows.

Begrudgingly, Dean slipped into the driver side and unlocked the doors.

“You don’t mind me riding shotgun, right? Those little love birds do like to cuddle, am I right?” Gabe said with a laugh.

Dean was a little surprised to find out someone in Jimmy and Castiel’s family knew about them. He’d assumed since their parents were unaware that they kept it from the rest of the family too. What unsettled Dean more was the fact that it seemed a lot like Gabe had no idea who _Dean_ was. He shook it off though and started the engine. Luckily it was still warmed up from the drive over.

“She really is pretty.” Gabe said as he ran his hand along the dashboard.

Okay so maybe this guy wasn’t _too_ terrible.

“Bet she’s seen a lot of action. Play your cards right and she could see a little more.” Gabe said with a leer so exaggerated that Dean couldn’t quite figure out if he was serious or not.

He half expected that it was a joke. It was fairly unusual for Dean to be hit on by men. Even though he never did anything to put off a certain vibe, people generally assumed he was straight. He was about to come out and ask whether Gabe was serious or joking when the back doors opened and a rather flustered set of twins slid in.

Jimmy tossed a coat over the back of the seat as Dean put the car in reverse.

“So…” Dean said, pausing briefly. “Someone wanna tell me where the heck we’re going?”

***

“Seriously? An arcade? What are you, twelve?” Dean asked as he looked up at the store front.

“You wound me Dean! I’ll have you know that when I lived here this was the hot spot. And it isn’t an _arcade,_ it’s a state of the art gaming facility. The collected technology in this building alone could be sold to feed an entire country for a year. Let’s go handsome.” Gabe said as he hooked Dean’s elbow. “Jimmy, Cassie. Run across the street and grab us some food, huh? Don’t forget the candy!”

Dean looked over his shoulder as Gabe dragged him in. Both twins shrugged, Jimmy grinned a little too much at Dean’s obvious discomfort, before they turned and walked to the store across the street. Dean glared at their backs right up until the doors swung shut.

“Okay hot stuff let me show you around.” Gabe said as he continued to keep a death grip on Dean’s elbow. “Over there are the classic games, air hockey, foosball, pool, darts, beer pong on Saturday nights if you’ve got a decent ID. That door back there leads to the VR wings. Over there is laser tag but that’s always reserved weeks in advance. And this room over here. Well this… this is my favorite. Rare classic arcade games that haven’t been out on the market for a couple a’ decades at least. I bet some of them still have my high sc- _Oh shit.”_

Awkwardly, Dean stumbled as Gabe came to a sudden stop. He looked over, concerned, to see Gabe had gone as pale as a ghost, his eyes wide and glossy.

“No, no, no. I thought he was gone, what the hell is he still doing here?” Gabe stammered.

Unsure of what Gabe was talking about, Dean followed Gabe’s stare and spotted a guy that looked a couple years older than them playing one of the shooter games.

“Hey Gabe.” Dean said softly while he tugged at Gabe’s arm but was unable to budge him. “Why don’t we go play pool ‘til Jimmy and Cas get back, huh?”

Gabe didn't seem to hear a word Dean said, only hoarsely said, “He’s supposed to be at college on the west coast.”

Unfortunately, whoever the guy was ran out of credits on the game he was playing and turned to head for another. Dean saw the moment he noticed them. The guy’s expression went from annoyed, likely ‘cause he lost, to breaking out in a twisted smile that was anything but friendly. He was good looking, with light blonde hair and icy blue eyes but Dean didn’t have to know anything about him to know that he was bad news. It practically flowed off him in waves

“Gabe! What the fuck are you doing here, man?” The guy asked, like he was greeting an old friend, but his face told a different story.

“L-Lucifer… I… I thought you were on the west coast now.” Gabe stuttered as he seemed to shrink before Dean’s eyes.

“Jesus man, you still payin’ people to hang out with your hideous faggot ass? Hope you got a good paycheck.” Lucifer nodded to Dean as he moved closer.

Gone was the louder than life guy that’d annoyed the crap out of Dean. In his place was a shaking shell that tried to make himself as small as possible. Dean was so focused on Gabe that he missed the tells and before he knew it Lucifer had yanked Gabe from Dean’s hand and spun him around to slam him hard against the wall.

Dean didn’t even think. He reached out and grabbed Lucifer, pulled him off Gabe.

"Keep your goddamn hands off my boyfriend you fugly closet case." Dean said in a low, threatening growl, with no plan other than putting this asshole in his place and getting that kicked puppy look off Gabe’s face.

For a second they both stood there and stared at Dean, open-mouthed. Then Lucifer’s face twisted and he lunged out as his fist flew.

“Dean!” Yelled Gabe.

Dean didn’t need the warning this time. He grabbed Lucifer’s swinging fist and twisted, used the momentum to twist his arm behind his back. Roughly, Dean gripped the back of Lucifer’s head as he pitched forward and slammed him face first into the control panel of the nearest video game.

With a grunt of anger, Lucifer shoved himself back and broke free of Dean. Cautiously, Dean backed up and waited, sure as shit this guy would be dumb enough to charge him again.

Like Dean could see the future, Lucifer ran at him and yet again Dean used it against him, twisted out of the way last second and hooked Lucifer’s ankle, sent him sprawling. Dean was on his back in a second, knee pressed into his spine as he slid his forearm around Lucifer’s neck. He yanked up and cut off Lucifer’s air supply.

Not only was this prick a nasty homophobe, he was a bully that picked on people smaller than him. Dean had no doubt the guy had done a number on Gabe at some point to have that kind of effect on him. And Gabe was Jimmy and Castiel’s family; messing with him was the same as messing with them.

A rage that Dean’d only ever felt once before, when he’d found out some kids had beaten up Sammy and stolen the money that Dean’d scraped together for a birthday present, bubbled up in Dean’s gut. He wanted this guy to never hurt another goddamn soul.

“Dean! Stop! He can’t breathe!” Gabe cried out frantically.

Dean looked up at Gabe and saw concern had pushed out the fear in his eyes. It cleared away the red fog that was making Dean’s brain hazy. He let up on Lucifer’s neck and stood while Lucifer gasped to fill his starved lungs. Dean gave one final kick to Lucifer’s side.

“If I _ever_ find out you’ve so much as laid a finger on Gabe again, you’ll be leaving in a fucking ambulance. Do. You. Understand?” Dean gritted out, his Texas accent out full force with his anger.

Lucifer nodded from the floor.

“Get up and get out. Before I change my mind.” Dean growled.

Lucifer scrambled to his feet and swayed a little before he managed to steady himself. 

“Get!” Dean roared.

Lucifer gave Dean one last terrified glance before he bolted for the front door. Luckily, no one had bothered to come check on the commotion. Dean turned to look at Gabe who was staring at him, wide-eyed and mouth agape.

“Hey Gabe. Man I’m sorry. Are you o-” Dean found himself cut off as Gabe shoved him backwards across the room.

For a moment, Dean was so confused about what was happening that he didn’t struggle, just let himself be pushed back. Suddenly, Dean was pushed against and through a swinging door. He stared around dumbly as he found himself in the bathroom. Just as he turned back to Gabe ready to ask what the hell he was doing, Gabe was suddenly on him, all lips and tongue and teeth.

Panicked, Dean pushed at Gabe as he backed away and pulled from his grasp.

“Woah, Gabe! I-” Dean protested.

Gabe was completely oblivious in his frenzied gratitude. Without warning he sank to his knees in front of Dean and tugged at Dean’s belt.

“Shit! Gabe!” Dean shouted, stunned.

“Holy fuck.” A voice gasped from the door.

Dean’s head whipped up as Gabe’s fingers stilled. The door was pushed open and two very surprised looking twins stood there, shocked. Jimmy finally broke the silence.

“We… we were just coming in when you guys went into the bathroom. We…” Jimmy said, he was clearly confused but needed to say _something._

Dean couldn’t take his eyes off of Castiel though. He watched as surprise twisted into anger and hurt before it became a blank mask, all emotions gone. Without so much as a word, Castiel spun on his heel and grabbed Jimmy’s arm, insistently dragged him with him while Jimmy tried to speak but was cut off by the swinging door as it slid shut with their departure.

Fingers clumsy in his haste, Dean scrambled to do up his zipper and belt, he hadn't even realized that Gabe had gotten it down. He stumbled over Gabe and out of the bathroom but Jimmy and Castiel were nowhere to be found. The bathroom door swung open behind him but Dean didn’t wait. He ran out into the lobby and scanned the area but the only person there was the guy manning the front desk.

Desperately, Dean headed for the front door and pushed it open just in time to see the twins as they slid into a cab. Jimmy shot Dean a look that he couldn’t read before the car pulled out. Crushed and hopeless, Dean turned around and sagged against the door frame. When he looked up Gabe was standing there looking forlorn.

“I… I’m so sorry Dean.” Gabe said.

“It’s okay man. You didn’t know. I’ll just… drive you back and talk to them. Maybe by the time we get there they’ll have cooled down a little.”

Unfortunately they didn’t. When Dean and Gabe got to the Novak residence one of the maids answered the door, something Dean hadn’t seen any of the times he’d been there. She let Gabe in but when Dean asked to come in he was told the Novaks weren’t “entertaining guests” and was handed his duffle followed by a door to the face.

_Fuck._

***

The ceiling in Dean’s room had a crack in it right above his bed that ran half the width of his room. Dean knew that intimately because he’d spent the last hour staring morosely at it. His chest ached and the shitty emo playlist he was listening to probably wasn’t helping but he felt like shit. Depressing lyrics echoed through his headphones into his ears as he replayed what’d happened over and over in his mind. Turned it a million ways to Sunday and tried to figure out how he could’ve done something different.

All he’d been trying to do was something nice for Gabe, and he’d ended up accidentally leading him on, and worse than that, Castiel and Jimmy’d walked in at the worst possible fucking moment and now _they_ weren’t talking to him. Frustrated, Dean ran a hand through his hair and tried not to picture the shocked, hurt look in Castiel’s eyes when he’d dragged a wide-eyed Jimmy out of the bathroom before Dean could even try to explain.

His heart squeezed in his chest, and all he wanted was to fix things with them, but how could he when they wouldn’t answer his calls or texts? He’d sent them each a half a dozen apologies and explanations, left way more voicemails than anyone who had a sense of pride would. And nothing. Not one word. It was worse than yelling, or crying or anything because Dean’s mind just kept offering up explanations; he’d fucked things up too badly, they didn’t care that Dean hadn’t actively participated, or that he’d tried to stop it. Or worst of all, maybe they’d finally figured out they didn’t need him and his bullshit anyway so, they didn’t want to hear from him. 

Dean’s eyes stung, and he blinked away the wetness in them, sighed out a breath, and wrapped his arms more tightly around his own waist, like that’d hold together the pieces of himself that felt like they were breaking. This couldn’t be it, Dean _needed_ Jimmy and Castiel even if _they_ didn’t need him. He... he loved them, damn it. Wouldn’t _hurt_ this fuckin’ bad if he didn’t.

He ground his palms into his closed eyelids, felt lost and so fucked. Absorbed in his own inner monologue, he barely heard the knock on his door and sat up just as Castiel walked in.

In a flash, Dean whipped off his headphones, “Cas!”

Awkwardly, Castiel gave him a little forced smile as he closed the door behind himself and shrugged one shoulder, “Hello, Dean. Sam, um, Sam let me in.”

Dean’s heart pounded in his chest, and he got to his feet. Only one reason Castiel would be there right now, wouldn’t just call or text him back. All of a sudden Dean had trouble breathing, like there wasn’t enough air in the room. _This can’t- this can’t be happening._

“I-I, Cas it wasn’t-” Dean tried to get the words out but they were too thick and he stumbled over them, couldn’t hold in his panic, “I- you gotta believe me, I never woulda-”

“Breathe, Dean.” Castiel cut him off, and Dean sucked in a harsh breath at the warmth in Castiel’s voice. _What?_ “Gabe already explained everything. I know it wasn’t your fault. Jimmy tried to tell me when I was dragging him away. I should have-”

Castiel didn’t get to finish his sentence, Dean suddenly found himself across the room, lips pressed to Castiel’s. He buried his hands in Castiel’s hair and breathed his relief into his mouth. When Castiel’s hands came up to comfortingly cradle Dean’s face, Dean thought his heart would burst with the gentleness of it. Gradually, the kiss slowed, turned less desperate. The way Castiel kissed him felt a lot like _I’m so sorry_ and Dean let it soothe him, melted into it.

Piece by piece they peeled each other’s clothes off between deep sensual kisses, completely focused on getting one another naked. On needing to reassure each other that they were okay.

Somehow they ended up on Dean’s bed with his back against the mattress while Castiel kissed him into his pillow. Dean’s hands couldn’t settle in one place, smoothed over Castiel’s back, down to grab his ass and pull his hips slowly forward, ground his hard, leaking, cock up against Castiel’s.

“Cas,” Dean breathed against his lips, felt so fucking good but had to keep quiet because Dad and Sam were just downstairs.

Hotly, Castiel hummed into his mouth and the sound of it reverberated through Dean, so perfect. Pleasure built up steady-slow between them. Castiel braced himself on one forearm by Dean’s head while his other ran along Dean’s neck, down his side and then pulled his thigh up until Dean wrapped his leg around Castiel’s waist. Pushed down harder against Dean, and that was Dean’s breaking point. His hand shot out and he stretched to reach his nightstand drawer. Managed to get it open and fumbled around blindly until his fingers found the bottle of Astroglide he kept there.

“Please?” Dean whispered, wrecked, as he passed it to Castiel; watched as his eyes darkened, full of lust and affection and Dean just wanted _more._

The lube cap clicked, and then a moment later Castiel shifted a little, reached down and- and nothing, Dean’s eyes were closed while he waited for that first hot slide of Castiel’s finger into him but it never came. Instead, Dean heard a slick-wet sound that sent a shiver down his spine and forced his eyes open.

Just before Castiel dropped his head down onto Dean’s shoulder and blocked the view, Dean got a brief glimpse of his finger sliding into himself. _Holy shit, he’s- he’s-_ Dean’s brain couldn’t even finish the thought, too hot. Castiel was fingering himself open, and they’d never done _that_ before, but Castiel was half on top of him, panting with exertion, so fucking sexy.

Without even thinking about it, Dean’s hand moved down to feel where Castiel’s fingers were sinking into his own ass. Found that he was already sliding two in, and as Dean’s fingers brushed along the stretched, slick, skin of Castiel’s rim, he let out this breathy little sound like nothing Dean’d ever heard him make before, so soft and hot that liquid fire burned in Dean’s veins.

“Can I?” Dean whispered, and pressed just a little with one finger to make sure Castiel understood what he meant.

A strangled breath broke free from Castiel’s chest as he nodded into Dean’s shoulder and that was so fucking sexy that Dean’s dick throbbed in sympathy. So slow, Dean slid his finger in alongside Castiel’s. And fuck, he was hot and wet with lube and Castiel’s mouth latched onto Dean’s shoulder to muffle the noises he was making.

Just quiet little grunts, but it was so fucking hot to think that Castiel couldn’t help making them. In tandem, their fingers worked inside him, slid in and nearly out together again and again, until finally Castiel pulled his fingers free and Dean followed suit.

There was a drawn out moment while Castiel slicked Dean’s cock up, where they just stared into each other’s eyes, and Dean held his breath because everything about Castiel was perfect. Then Castiel straddled his hips and lined Dean’s cock up, sank slowly down onto him.

“Fuck, Dean.” Castiel sighed when he bottomed out, bent himself forward to kiss Dean. Lips and tongue fierce and gentle at the same time and _God_ he felt so fucking tight and hot around Dean’s cock.

So damn good that Dean’s head dropped back and he bit his own lip, had to, to keep himself from moaning loud when Castiel slowly started to ride his cock. A second later Castiel’s mouth was back on his in a messy kiss while he gradually built up to a faster pace. Careful not to make Dean’s bed squeak, Castiel dropped down onto him over and over again.

Pleasure resonated relentlessly through Dean, a slow, steady climb that left him breathing heavily against Castiel’s mouth while his hands smoothed over every bit of Castiel’s skin that they could reach. Like he couldn’t get enough of him, needed him, _God,_ he fucking needed him. Loved him so fucking much it _hurt._

Castiel’s face screwed up in a combination of concentration and pleasure and he looked like he was barely holding himself together. Dean’s body drew taut, his hips twitched involuntarily up and tried to bury his cock deeper inside Castiel. So goddamn _close._

And then Castiel pulled back just far enough to look Dean in the eyes. His hips never stopped and his breath was hot against Dean’s lips as he murmured, “Come in me, Dean. I want to feel you come inside me.”

“Fuck,” Dean groaned softly before he cupped the back of Castiel’s neck and pulled him down into a passionate, eager, kiss. Pushed up into him twice more before his hips stuttered and he came, so fucking hard, inside Castiel with a drawn out hiss of his name. Castiel ground down onto him, worked him through his climax, so fucking hot.

Before he could pull off, Dean reached between them and fisted his hand around Castiel’s cock, slick with precome, jacked him rough and fast. He could tell by the way Castiel’s hips jerked that he was close and he slid his thumb over the sensitive head of his cock. God, he was hot like that with his eyes shut tight, chest heaving, body locked up tight.

A few more hard quick pumps of his fist and Castiel came, breath held, with a shudder. Pulsed white stripes of warm come over Dean’s chest and stomach then gasped in a desperate breath of air as he collapsed forward onto Dean, heedless of the mess between them.

For a long time, they just laid there and caught their breaths. Eventually Dean softened enough that his cock slipped out of Castiel, which was right about when Dean decided they ought to clean up a bit before he ended up sleeping in extra crusty sheets that night. It’d probably be suspicious as fuck when Castiel left if he went to wash them.

So, Dean wiped himself off with a random t-shirt he found on the floor, which was partially covered in dirty laundry. He hadn’t expected anyone to come over and at that moment he was pretty glad of it. He grabbed another one off the floor and wiped Castiel down too, then tossed them on the floor again.

Castiel moved Dean onto his back, tucked himself against Dean’s side and pulled the blankets up over them. Wound up with his head on Dean’s chest, arm wrapped snuggly around Dean’s waist.

“That was fuckin’ awesome, Cas, don’t get me wrong, but ya know you didn’t have to do that right?” Dean said softly into Castiel’s hair.

He felt Castiel smile against his chest, “Dean, it’s not like I’ve never been fucked before. And I enjoyed it very much.”

Relieved and happy, Dean grinned too, “Yeah, I could tell.”

The quiet sounds of their breathing filled the room, and Dean carded his hand gently through Castiel’s hair, full of affection for him. Another wave of relief washed over Dean mixed with gratitude because he knew exactly how damn lucky he was to get to hold Castiel like that.

“When Gabe was a freshman,” Castiel said, broke the silence without any preamble, “Jimmy and I were still in middle school. We had no idea at first what was happening with him, why he’d become so withdrawn. Jimmy-”

Castiel paused to take a breath, like this was hard to remember, painful, “Jimmy was the one who pried it out of him. At the beginning of the year, Gabe had made the mistake of flirting with Lucifer in front of his friends. Gabe has excellent gaydar. No way he was wrong about what he saw in Lucifer. Long story short, Lucifer spent the next two years beating Gabe up any chance he got. And Gabe… Gabe refused to tell his parents because his father is a bigot. He was so scared of what he’d do that he’d rather put up with Lucifer’s torture. Can you imagine that? How frightened he must’ve been?”

Castiel’s head tilted back so that could meet Dean’s eyes, and Dean just shook his head, horrified. Sure, John probably wouldn’t be happy if he found out Dean batted for both teams, but he wasn’t afraid he’d hurt him or kick him out or anything _really_ , really bad. He didn’t _think_ so anyway. Though he hadn’t told John. Dean pushed those thoughts away for now.

“In the end,” Castiel bit his lip and laid his head back on Dean’s chest, “Jimmy and I went to his parents after Gabe almost ended up in the hospital. We were terrified for him, and we couldn’t keep pretending that nothing was wrong. Someone needed to do something. We told my aunt about Lucifer and Gabe. When his dad found out, he lost it. Said he was going to send Gabe to conversion therapy…”

 _Jesus,_ Dean’s eyebrows shot up, and his hand stilled in Castiel’s hair before he forced himself to keep moving it soothingly.

“Thankfully, my aunt wouldn’t let him do it. She left my uncle and they moved where Gabe could get away from Lucifer because he wouldn’t go to the cops…”

Castiel trailed off, and Dean hugged him closer while what he’d said sank in.

 _“Jesus.”_ Dean said softly, “Guess that’s what happens when you name your kid _Lucifer._ Who the hell _does_ that?”

“His name’s actually Nick. Lucifer’s just a nickname he picked up in middle school, but it says something about him that not only did it stick, but he actually _likes_ it. He doesn’t deserve to breathe the same _air_ as Gabe. I- Dean, what you did for him… Standing up for him like that… It meant a lot to Gabe, and to me and Jimmy as well.” Castiel paused for a beat and Dean was about to say it was nothing, just what anybody would do, but then Castiel spoke again.

“The, uh, the reason… that I didn’t stop to find out what was going on when we walked into the washroom… It’s because I realized I was in love with you, Dean. And I thought, if you- you, well then it wasn’t real for you, and it hurt too much. I couldn’t be rational.”

Dean’s heart felt way, way, way too fuckin’ big in his chest; Castiel _loved_ him.

“Cas, you gotta know I’d never do something like that. I-I love you… Jimmy too.” Dean confessed, and Castiel let out a warm chuckle, tilted his head back to look up at Dean again.

“Maybe we’ll just pretend you didn’t say that last part so that Jimmy hears it from you first.” Castiel said with a small smile, eyes lit up with happiness.

“Yeah,” Dean agreed with a rueful grin, “Speaking of, not that this wasn’t _awesome,_ but… I kinda feel guilty that Jimmy’s not here too.”

Castiel’s lips tugged down in an adorably confused frown, “Why? You know Jimmy and I still enjoy an active sex life when it’s just the two of us. This isn’t any different.”

Instantly Dean’s eyes flashed to the ceiling and stayed glued there, because yeah, it kinda was, “Except it _is_ different, Cas. You and Jimmy came first. I don’t expect to be on the same level.”

“Dean, look at me.” Castiel demanded and Dean somewhat reluctantly complied, “Just because Jimmy and I have loved each other longer doesn’t mean we love you any _less.”_

Dean bit his bottom lip, chest tight with emotion and then Castiel pushed up to kiss him, their lips collided in a warm brush, full of so much meaning that Dean ached with it until Castiel abruptly pulled back, “Not that I’m saying Jimmy’s told me he loves you… I wouldn’t say that… that should come from Jimmy, of course.”

“Of course.” Dean echoed with a wide grin before he kissed Castiel one more time, slow and sweet and easy.

Later, after Castiel had gone home, Dean couldn't stop smiling. Castiel _loved_ him. Jimmy did too, even if he hadn't told him so yet. He couldn't wait to tell Jimmy he loved him and hear him say it back. Then everything really would be perfect.


	11. Chapter 11

Dean ended up sticking around for brunch, after Castiel slipped out and headed home. When they finished Dean loaded up the car with his and Sam’s duffel’s and they said a quick goodbye to Dad before they headed out for the week. Sam was staying with Kevin, and Dean was going to spend the week with Castiel and Jimmy. He’d just told Dad he was gonna crash at his friends’ place for spring break and Dad’d seemed happy that he’d settled in so well here. Thankfully no one questioned why Dean had come back when he was supposed to have been gone yesterday.

Dean was kinda nervous about Dad being alone for so long, but he probably needed a break from them now and then, and he must’ve noticed Dean’s hesitance because he told Dean that Uncle Bobby was actually coming to visit for a few days, so he’d have some company. Which really went a long way toward reassuring Dean because Bobby was always a good influence on Dad.

The drive to Kevin’s was pretty subdued. Sam was fairly excited about some science experiment Kevin’s mom had planned for them to do. It was an extra credit project for Kevin that Sam was just pumped to tag along with for no other reason than that he loved learning. All kinds of dorky, but Dean thought it was kind of adorable that Sam was such a nerd.

When Dean dropped him off, Sam surprised him with a hug before he jumped out of the car to grab his bag. Dean smiled as Sam jogged up to the door and waved as it opened. Once Sam was safely inside, Dean drove back down the driveway and headed to Jimmy and Castiel’s.

Last night he’d been so damn ready to tell Jimmy he loved him, but this morning it seemed kinda daunting. Not that it was any less true, but just that… With Castiel, it’d been an in the moment sort of thing, and Castiel had said it first and- and it was just _easier,_ in the afterglow, to admit his feelings.

Dean stewed about it on the way over, wondered whether he should just come out and say it, or maybe if he should do something special for Jimmy. Gabe being there definitely threw a monkeywrench into any ideas Dean had for doing something special.

Turned out Dean was right, Gabe being there was definitely an impediment to getting some alone time with Jimmy, but it also turned out he was a pretty cool guy. Now that he wasn’t hitting on Dean every five seconds, he had the chance to get to know him.

He was actually kinda funny, and he brought out a more playful side of Castiel that Dean hadn’t really gotten to see yet. Which was pretty awesome. They spent the morning playing video games, and when Gabe eventually got bored of sitting still for so long, he decided that paintball was the perfect way to spend a Sunday afternoon.

Dean wasn’t entirely sure about it, but it’d been too hard to say no to everyone else’s excited faces. So they spent the rest of the afternoon out in the massive wooded area behind the twins house shooting at each other much too competitively. Dean and Jimmy had teamed up against Castiel and Gabe and by the time dusk had fallen there was no clear winner, but a lot of sore bodies and happy grins.

After quick showers and an easy supper courtesy of the kitchen staff, they marathoned the BBC’s Sherlock until one in the morning because Gabe insisted that they needed to see it after he’d been thoroughly disgusted to learn none of them had watched it.

He probably would’ve made them watch the whole series, which Dean honestly wouldn’t have minded because it _was_ good, and Sherlock was hot, but the day’s exertions caught up with them and Jimmy had fallen asleep on Dean’s chest, with Dean’s arm snug around his shoulders. On Dean’s other side, Castiel looked about ready to do the same.

Dean yawned, then spoke quietly as the credits for the episode they’d just watched rolled, “Maybe we should call it a night, guys? Jimmy’s already out and I’m beat.”

“Mmm.” Castiel hummed, “I’m tired as well.”

“Fine.” Gabe grumbled before he lost his battle with a yawn, “If you losers are too lame to binge watch the whole series in one night, we’ll just have to watch more tomorrow night.”

“Eh, sounds good to me.” Dean said easily as he ignored the losers comment.

They all made their way upstairs, and parted ways at the doors to the twins’ rooms. Gabe headed into Jimmy’s room where he’d been staying since he’d arrived. Tons of rooms in the house he could’ve had his pick from, but Jimmy had told Dean that he’d made Gabe take his since he’d sleep in Castiel’s room anyway. Might as well stay in the coolest part of the house, Jimmy’d said.

Dean followed Castiel and Jimmy into Castiel’s room where they took turns in the bathroom to get ready for bed. Any hopes Dean’d had earlier in the day of ending things with a bang were long forgotten. His body ached, littered with bruises and his brain was fuzzy with exhaustion. The three of them just crawled into Castiel’s bed and fell asleep in a jumble of intertwined limbs.

The next morning Dean woke up to warm hazy pleasure washing through him. One set of lips mouthed hotly at his neck, just beneath his jaw and another trailed slick sucking kisses along his hipbone.

“Mmm.” Castiel breathed, “Morning.”

His tongue slid along the shell of Dean’s ear and Dean shuddered, sucked in a deep breath as Jimmy’s lips skated so close to the base of his dick that Dean ached with it.

“Morning. _God.”_ Dean groaned softly, felt so damn good.

One of his hands moved down to push through Jimmy’s hair, and the other pulled Castiel into a kiss by the back of his neck. So sexy, the way Castiel’s tongue slipped fluidly into his mouth at nearly the exact same time Jimmy sucked his way up the underside of Dean’s very hard cock.

Got to the head and laved his tongue over it. Dean’s hips twitched with the effort not to buck up into the warm wet heat of Jimmy’s mouth as his lips closed around him. Instead, he threw his head back and let out a groan as Jimmy sucked him all the way down.

“God, I love your mouth.” Dean said heatedly, and his heart beat double time for a second when he almost followed it up with _God, I love you._

Kept those words back though, because Jimmy deserved better than to hear them for the first time in the middle of a blowjob. But Dean’s chest swelled with the truth of it all the same.

Relentlessly, Jimmy’s fucking talented mouth worked up and down Dean’s cock over and over. Heat and lust filled up every inch of Dean’s body. So damn close and just as his body locked up, just as he started to come, spilled into Jimmy’s mouth-

Castiel’s door banged open, “Hey losers, can’t believe you slept in this- Oh, shit!”

Dean’s eyes went comically wide, and Castiel yanked the blanket right up over Jimmy’s head. Jimmy made a muffled choked sound that might’ve been a laugh, might’ve been surprise before he pulled off Dean’s dick with a cough.

“Guess I should’ve knocked…” Gabe said awkwardly. “Oops.”

“Gabe,” Castiel said calmly, “Get out.”

“Yeah…” Gabe agreed with a grin, “Should probably do that, shouldn’t I?”

“Yes.” Castiel answered and Jimmy was _definitely_ laughing under the blanket now.

“Fine, but don’t take long, I already told the driver to get the limo ready. I’m bored.” Gabe complained as he turned and walked out of the room, closed the door behind himself.

And that was basically how the first half of spring break went. Not a spare moment to relax because Gabe always had something fun yet exhausting planned for them to do, followed by netflix binges and morning wake-up calls to do it all again.

By the time Thursday rolled around, the day Gabe was leaving, Dean was almost relieved. Don’t get him wrong, he liked Gabe fine, he was just tiring to spend so much time with. Full of energy, mind going a mile a minute and basically never needed a break. Downtime was a thing he didn’t really do, unlike Dean.

Still, Castiel and Jimmy were a little sad to see him go, and Dean had to admit, he was too. A little tiny bit. Very tiny. Infinitesimal really. Okay, fine, he’d miss the guy. But plus side, he had three more days with Jimmy and Castiel. Uninterrupted days. And fuck was he ever looking forward to those.

Of course, that also meant he wouldn’t have a buffer anymore, and by that Dean meant, he’d have time alone with the twins and he’d have to admit to himself that Gabe being around all the time _wasn’t_ the deciding factor in why he hadn’t told Jimmy he loved him yet.

Dean’s own dumb nerves were now fully responsible for that fact. What the hell was he so scared of? He knew Jimmy loved him, could feel it. He knew he sure as hell loved Jimmy, but it was like some kinda mental block when he tried to tell him. Felt like they should have some kinda big romantic moment.

Which was stupid, because with Castiel it’d been so natural, just an emotional confession in their afterglow, but Dean was still stuck on the idea anyway. Thought there had to be a perfect moment for him to say it.

After Gabe left, the rest of their day was pretty relaxed. They hung out around the house, played video games and ate way too many snacks. Like they were catching up on rest after being on the go all week, they called it an early night after Dean kicked Jimmy’s ass one last time in Soul Calibur V.

They settled into a now familiar routine and moved fluidly around each other as they got ready for bed. Ended up cuddled together in Castiel’s bed again, Dean in the middle. Wiped out, Dean didn’t take long to fall asleep.

***

Luxuriously, Dean stretched out in the soft warm bed as he came awake. He felt Castiel, who’d fallen asleep on his left, snuggle in deeper as the movement jostled him. Dean smiled and reached out to pull Jimmy into him but found only empty bed.

“Jimmy?” Dean mumbled as he tried to force his eyes to open against the morning light.

After he blinked a few times, Dean pushed himself up to sitting and looked around the room until his eyes landed on Jimmy.

“Umm… Cas?” Dean said and reached behind himself to nudge his still sleeping form.

Castiel mumbled sleepily as he uncurled and stretched. Concern caused Dean to extricate himself from the bedding and slide down to kneel in front of Jimmy.

With his legs slightly spread, Jimmy knelt, back straight, head bowed slightly and arms clasped behind his back. Dean caught a glimpse of a black leather collar spread just in front of Jimmy’s knees on the floor.

“Jimmy?” Dean asked cautiously as he leaned forward to catch Jimmy’s gaze.

He couldn’t though. Jimmy’s eyes were glazed and unfocused, almost dreamlike. They didn’t so much as shift when Dean came within his eyeline.

“Cas, I think there’s something wrong with Jimmy.” Dean said as panic started to rise in him.

“Oh.” Castiel said softly from the bed. “Dean come here.”

Reassuringly, Castiel reached a hand out to Dean. Dean took it, reluctantly left Jimmy’s side.

“Did you read anything about subspace when you were looking things up?” Castiel asked as he ran a soothing hand on Dean’s back.

“Umm… I think I saw it but didn’t really read anything about it.” Dean said, he wished he hadn’t panicked and avoided doing more research.

“It’s a headspace that subs get into, usually for more intense play. Even the most submissive person has instincts to refuse, or react to things adversely. Push back against their Dom. When a sub trusts their Dom fully they can slip into a space that leaves them completely pliant and at the mercy of their Dom. That’s when it’s up to the Dom to know their sub inside and out and take care of them. Being in that headspace can make it hard for a person to make rational decisions sometimes, not safeword when they should.”

Dean nodded to indicate his understanding. He felt threads of desire as they began to pulse through him, though he was surprised that it came from both the thought of someday reaching a place where he could give himself over so thoroughly as well as what Castiel must feel to have so much power put in his hands.

“Dom’s also occasionally go into their own headspace, although not nearly so deep as their subs. It’s imperative that Doms stay aware enough to control the situation, ensure the wellbeing of their subs. But that feeling of absolute power, it can be almost dizzying, make you feel bigger than life.”

Castiel slid to the edge of the bed and stood, pulled Dean up with him.

“Jimmy must have woken up needing to be thoroughly dominated. He won’t be the Jimmy you’re used to when he’s like this. That beautiful, bratty little sub doesn’t exist, in his place is an equally beautiful sub, pliant and perfect.” Castiel said as he ran his fingers through Jimmy’s sleep mussed hair.

And truthfully, Dean had to admit that there was something beautiful about it. Such stillness in Jimmy, someone who was constantly in motion with a mind that never seemed to stop. The way his skin rippled over flexed muscles as he held that strange position, skin golden in the morning light. Dean couldn’t resist reaching out to join Castiel’s fingers as they caressed Jimmy’s hair.

Briefly, Dean hesitated and looked to Castiel, who nodded slightly, before he carded his own fingers through the tousled locks. There was an almost imperceptible shift that indicated Jimmy was restraining himself from moving into the touch.

“Good boy.” Murmured Castiel.

Dean shifted back a little to get a better look at the twins. God, they were beautiful. He was more than a little excited to watch the two of them in this dynamic.

“What now?” Dean asked as he repressed the urge to reach down and stroke himself.

“Now? Now, I make him ask for it.” Castiel said with a captivating smirk.

Completely enthralled, Dean watched as Castiel took a step back until his thighs bumped against the edge of the bed.

“Jimmy. Present your collar to your Dom.” Castiel commanded.

His words and tone went straight to Dean’s cock. Jimmy reacted instantly, released the grip he had on his wrist and reached for the collar. He grasped each end and held it up above his head without lifting his gaze from the floor. For a minute Dean felt completely lost. He looked down at the butter soft leather stretched between Jimmy’s hands.

Not held in front of Castiel, but in front of _him._

“I… I don’t… what?” Dean asked as he looked back and forth between the collar and Castiel.

A soft smile tilted up the corners of Castiel’s lips and his blue eyes sparkled warmly.

“Dean, do you prefer Sir or Master?” Castiel asked.

Stunned, Dean was pretty sure he stopped breathing. He couldn’t help but stare at the collar, like it would jump up and bite him if he took his eyes off it.

“Cas… I… I…” Dean stammered.

The smile on Castiel’s face slipped into an expression of concern. His eyes flicked to Jimmy before they moved back to Dean. He swiftly grabbed Dean’s hand, pulled him, and not gently, from between Jimmy and the bed over to the other side of the room.

“You need to control yourself Dean. It’s imperative to Jimmy’s state of mind that you put off an air of confidence.” Castiel bit out.

The hard look he was giving Dean softened as he took in the panic in Dean’s eyes.

“I’m sorry, that was harsh. But Jimmy is _incredibly_ vulnerable right now.” Castiel whispered. “If you don’t want to do this, that’s more than okay. We’ve never discussed it. Usually I can see the signs that Jimmy’s getting ready to slip into subspace but I think it caught us both by surprise. So, _please_ don’t think anyone will be angry with you if you don’t want this. I’m happy to take care of him instead. But if you do, Dean. If you want this, you _have_ to commit to it. No waffling or going in and out of Dom mode. Do you want this?”

"I do..." Dean said hesitantly, then looked over at the submissive form of his gorgeous boyfriend with the warmth of love and awe in his eyes. _Man,_ did he want this. "I just don't know what I'm doing. I… I don't wanna hurt him, Cas."

Tears were forming in Dean's eyes from his conflicting emotions and Castiel reached up to brush a thumb across Dean’s cheekbone before he leaned in and kissed Dean’s trembling lips.

"Don't worry, Dean. I'm right here. I promise. You take care of him and I’ll take care of you _both."_

Dean took a steadying breath before he nodded.

“What do I do?” Dean asked.

Castiel couldn’t help but smile as he saw Dean physically flow into the role without conscious thought.

“Of course, Jimmy likes to be told what to do. And he likes it rough. You know that already. It’s just, more so, when he’s like this. Don’t ask him for anything. Tell him. He also likes humiliation.” Castiel said, fully prepared to go on but stopped when Dean interrupted him.

“H-humiliation?” Dean asked, some of his confidence slipped noticeably.

“Yes, mostly name calling. Come slut, whore, etcetera. But also physical degradation, although that’s more limited to things like boot licking and such, not the more public forms of degradation.” Castiel listed things off as casually as he would a grocery list.

“Cas… I don’t think I can do that.” Dean said as he glanced over at Jimmy again. “I know it’s what he wants but… I can’t say something like that to someone I lo-... to him.”

“That’s fine Dean, it definitely takes some getting used to. Don’t forget, Jimmy and I were able to ease into all of this together. You’re getting thrown into the deep end.” Castiel said comfortingly.

“Yeah but you’re gonna be my life jacket, right Cas?” Dean asked with an almost shy smile.

Castiel’s lips quirked in a bit of a smirk and then he continued matter of factly, “He also loves impact play. When he’s not in subspace we usually stick to spankings, occasionally a paddle but when he’s in subspace it’s usually more intense. We’ve got floggers, a whip and a cane, though the whip and the cane I’d probably prefer you at least observed before you used as they can both be damaging if not wielded properly.”

Dean suddenly flashed back to when Castiel tried to tell him all about his research right before they both speared Jimmy’s ass in the locker room. He’d been less than interested in the clinical details then but now he couldn’t help be grateful. Castiel did what he did, was the way that he was, because he would never do anything with or to either Dean or Jimmy without being certain he wouldn’t hurt them… at least not in a way they didn’t want.

Still, Dean was in pretty far over his head and all the clinical talk in the world wasn’t gonna kill his uncertainty.

“So what, I just start hauling off and… hitting him? Or… I mean isn’t that usually something used as punishment?” Dean asked as he followed Castiel across the bedroom.

They stopped before a beautiful armoire made of some sort of rich dark wood, polished to a warm glossy finish. Dean watched as Castiel reached for a raised piece of the carving along the side of the furniture. He slid the wood aside and revealed a small black square. Dean gawked as Castiel pressed his thumb to the square and the quiet of the room was broken by the mechanical click of a lock as it released.

“Damn, Cas, that’s like some next level spy shit!” Dean said, clearly awed.

“Well we definitely don’t need anyone else getting into this and I don’t always have pockets to carry keys in. Leaving one laying around would be counterproductive. I’ll have the technician schedule an appointment to add your thumb print as well.” Castiel said as he reached for the wrought iron handle.

“You don’t have to…” Dean trailed off as his jaw nearly hit the floor.

The armoire was stocked with tray after tray, and if the rest were anything like the one that Castiel pulled out it was probably one of the best stocked sex toy cabinets on the planet. The tray in question was lined in some sort of black silk or satin and lined up neatly across it were several dangerous looking implements, the ones Castiel had mentioned already and a couple Dean didn’t recognize.

Castiel trailed his fingers across them all before he hesitated over couple of floggers, one dark and black made of braided leather and one that just had individual strips of a soft brown looking material.

“I think one of these would be your best option. This one is leather, the falls are braided which makes them thicker and a little stiffer. It gives a nice sting but there’s very little risk of actually breaking skin unless that’s your goal.” Castiel shifted his hovering hand over to the one with the brown strands. “This one is a very soft suede. We mostly use it for sensual play when Jimmy’s ready to start coming down from some of the more intense impact toys so that the transition isn’t too sudden. But it can still cause the sting Jimmy will be looking for if wielded with that intent. There’s zero risk of injury with this one, though it isn’t nearly so intense as Jimmy usually anticipates.”

Hesitantly, Dean reached out for the toys before he pulled his hand back. He glanced over at Jimmy, still as unmoving and beautiful as a greek marble. His first instinct was to go with the suede, remove all risk, but he knew it wasn’t quite what Jimmy wanted and that made Dean unsure.

“Umm, do you think…” Dean swallowed hard, not entirely confident about how he should proceed.

“Dean, anything you ask of me, whatever you need I’ll give you so long as it doesn’t unnecessarily risk your’s or Jimmy’s well being. Please don’t be afraid that I’ll think less of you.” Castiel said, his brow creased in concern.

How did he always know just what to say?

“Could you… use them on me first?” Dean asked. “Not like… full on whip me ‘til I come. Just… I wanna know how hard to hit and what he’s gonna feel before I do anything to him.”

Castiel’s concern melted into a soft smile.

“Dean, I don’t think you realize how rare it is for a Dom to come right into the thought of putting themselves in a sub’s position. Most enter in thinking themselves too powerful, too unwilling to submit. Some, albeit bad ones, even believe they’re above submitting to anyone. The fact that your first thought is to know what he feels, to know what you’ll do to him tells me that you’ll make a wonderful Dom for him.” Castiel reached a hand up, curled it around the nape of Dean’s neck and pulled him into a soft kiss.

When Castiel moved away again he nodded over to the nearby bed post before he grabbed the two floggers.

“Go hold onto the post and present your back. Try to relax. Jimmy will be completely pliant when you do this and the sensation is entirely different if the muscles beneath the skin are tensed up.”

Instantly, Dean moved to comply, eyes glued to Jimmy as he wrapped his fingers high on the post and took a few fortifying breaths.

“Good boy.” Dean heard Castiel murmur from behind him. “The suede flogger first. The first couple of strikes will be gentle, the next much harder. Still, it won’t be too intense.”

Knowing that what was coming wouldn’t be too intense, Dean was able to settle quickly. The first strike came and it sent shivers along each nerve ending as the soft material landed on his skin, almost a caress. Castiel followed it up with two more strikes and Dean could see how these touches could have their use, could imagine being brushed with the almost silky strands to calm his skin after it’d spent time being more harshly abused.

“Ready for a little bit more?” Castiel asked softly.

He understood why Castiel was being so cautious and undemanding. Domming Dean wasn’t the role Castiel was there to play. But, it would’ve been so much easier if Castiel just ordered him around like he usually did, told him to shut up and take it. Didn’t leave Dean with any more control than his safeword allowed.

This wasn’t about _Dean_ submitting, though. It was about Jimmy. About Jimmy putting his trust into Dean’s hands when he’d only ever given that trust to one person his whole life. Dean would’ve been lying if he said that didn’t shoot straight to his cock… and his heart.

“Yeah Cas, I’m ready.” Dean murmured, hands only just barely tightened on the post as he continued to watch Jimmy.

The next strike had a little sting to it. Zipped along his flesh and pooled low in Dean’s gut. Barely more than a slight bite, there and gone. There were likely marks across his back but nothing that would last. Two more sequential strikes were enough to build up a tiny bit more and Dean could see the appeal. He could go at Jimmy for a while with this one, work him over, without having to worry about screwing up and doing any damage.

Cool fingers brushed across the warmed skin of Dean’s back, smoothed it with gentle strokes and Dean’s eyes drifted shut.

“Are you okay with trying the leather?” Castiel asked. “It’s completely okay if you’d rather just used the suede and leave the leather for another day.”

“No… I… wanna feel the leather.” Dean said as heat rose in his cheeks.

Truth was, it was only maybe half about wanting to be more comfortable with doing this to Jimmy. Dean’s cock was rock hard in the pajama pants he’d slipped on before they crashed last night. Dean fought hard to stay in the moment, in the mindset that this was what _he_ would be doing but his desire to explore being on the receiving end of more of those toys he’d caught a glimpse of was hard to ignore. Even if some of them looked wickedly dangerous and downright terrifying. Hell, maybe that was part of the appeal.

From the corner of his eye, Dean caught movement as Castiel set the suede flogger down on the bed. Then there was a soft whistling sound and Dean’s brain filled in the image of Castiel doing a couple of practice swings to gauge his speed.

“Cas.” Dean started, then paused. Castiel stayed quiet, just let Dean find his words. “No practice strikes, kay? Just… let me feel what Jimmy wants.”

“Okay, Dean.” Castiel said before he ran another soothing hand across Dean’s back.

Slowly Castiel’s warm touch left his skin and Dean was surprised that the tension he’d been fighting didn’t immediately come rushing back. The quiet whistle sounded again and Dean’s nerves lit up like the Fourth of July as lines of stinging pain striped his back. Dean cried out a mix of pain, surprise and almost desperate arousal. In reaction, there was the tiniest of breaks in Jimmy’s motionless state. Just the barest of twitches and a sigh so soft Dean would’ve missed it if he hadn’t been watching Jimmy so intently, almost like Jimmy had felt the strike himself.

Dean had a moment to take in everything he was feeling. The sting on his back was most obvious and not fading nearly as quickly as the strikes from the other flogger had. On the front of his pants there was a damp spot that'd rapidly grown where his leaking cock had caused the material to cling tightly to his skin. But the thing that caught his attention most was this electrified buzz that hummed over every inch of his skin. Like every touch he’d known up until that moment was suddenly dulled and somehow _less._

“Dean?” Castiel questioned softly at his ear as a firm hand came to rest on the back of Dean’s neck.

Startled, Dean realized where the concern he heard in Castiel’s voice was coming from as the buzzing in his ears grew louder and Dean finally noticed he’d been holding his breath.

“ _More.”_ Dean gasped as he forced the breath from his lungs.

Darkly, Castiel chuckled, huffed warm breath over Dean’s ear that sent shivers down his spine.

“I can’t _wait_ for the chance to have you truly under my hand Dean. I’m quite certain I could make you come purely from pain with how responsive you are.”

Forget waiting. Dean was almost certain he might just come in his pants right then and there, something that Castiel might've threatened in the past but not something Dean’d actually done since he’d gone through puberty.

“Another time I think.” Castiel whispered, then sent a shock through Dean’s system when the wet tip of his tongue dragged hotly down the edge of Dean's ear. “Once more.”

Before Dean had a moment to come back to himself, Castiel had moved away and the telltale whistle sang through the air. Dean’s back lit up again and this time Dean did his best to hold back his cry, able to anticipate it better. He breathed through the sensation and willed back the pleasure that coiled up in his gut.

_Jimmy… this is about Jimmy._

Castiel clucked his tongue just out of Dean’s eyeline.

“Of course when you’re submitting to me there will be none of that. Unless I tell you otherwise, you _will_ let me hear every single little sound.”

“ _Yes, Sir._ ” Dean managed to whisper before he pried his fingers off the bedpost.

After he gave Dean a moment to collect himself Castiel approached him holding both floggers.

“Which will it be?” Castiel asked.

There was no judgement, no leading expressions or posture. Dean had no doubt that Castiel would be happy with whatever choice he made. He was still tempted to go with the soft suede, the least amount of chance to fuck things up. But having felt them both Dean couldn’t imagine even a little bit that Jimmy, who was clearly used to this kind of thing, would get what he was seeking out of the lighter touch. He reached out and gingerly plucked the leather flogger from Castiel’s hand.

“As for how to go about it.” Castiel said as he walked back to the open armoire. “It’s up to you.”

When Castiel came back to Dean’s side he spoke quietly, for Dean only.

“Jimmy enjoys the pain regardless. So if you just want to use it as a sexual stimulant that’s more than acceptable.” Castiel said as he watched Dean take a couple of practice swings into his own palm. “However, if there’s something to be punished for then after the pain comes added endorphins from being forgiven.”

Absently, Dean nodded as he tried to sort his thoughts. A little bit of worry started to nag at Castiel but Dean’s posture abruptly shifted. His shoulders set and his face became resolute. Castiel had to stop himself from interfering when Dean turned and walked over to Jimmy.

He wasn't nervous for Jimmy, just anxious in general. No one else had ever been granted this much trust from his brother and though Castiel trusted Dean implicitly, he still couldn’t help but worry. This was new for Dean but giving up power over his brother, even just a little, was new for Castiel too.

Dean moved to stand in front of Jimmy and set the flogger down on the unmade bed. He took the collar from Jimmy’s outstretched hands and examined the clasp for a moment before he reached down and used the tip of his index finger to nudge Jimmy’s head up.

“Look at me Jimmy.” Dean said in a soft but firm voice.

When Jimmy did, something unknotted in Dean’s belly. Jimmy’s eyes were still hazy but there was love and, more intoxicating, absolute trust in them. Dean slid the leather around Jimmy’s neck and clasped it.

“Check the fit. You should be able to slip two fingers in all around.” Castiel said softly.

Immediately, Dean did as Castiel instructed and enjoyed the slight tremor he felt from Jimmy as his fingers slid around, touched the delicate skin of Jimmy’s neck. Satisfied that the collar was as it should be, Dean shifted his hands to Jimmy’s shoulders. Gently massaged the muscles that had been straining while he’d held the collar up.

“I’m sorry I made you wait so long… pet.” Dean said, voice still low but even, only slightly hesitant when he tested out the name. “You can call me Sir. Do you understand?”

“Yes, Sir.” Jimmy said immediately.

“Now, the reason I had to make you wait so long is because Castiel and I had some things to discuss. Do you know why we had to have a discussion?”

“No, Sir.” Jimmy said and Dean caught a flash of uncertainty cross Jimmy’s face.

“What’s my number one rule when it comes to having me try new things, pet?” Dean asked, his voice hard.

Realization flashed across Jimmy’s face, and Dean felt both pleased that Jimmy had picked up on it so quickly even in his current state and a little guilty when something close to shame settled in Jimmy’s glassy eyes.

“We talk about everything first, make sure you’re comfortable with it, Sir.” Jimmy said, and Dean could tell he was struggling not to lower his eyes.

“And did we discuss me Domming you, _pet?”_ Dean went against his natural instincts and let a little bit of bite slip into his tone.

He might’ve been concerned that he was being too cruel already if it weren’t for the fact that he noticed another minute tremor go through Jimmy.

“No, Sir.” Jimmy answered.

“Now.” Dean stopped massaging and cupped Jimmy’s face with one hand. “Lucky for you I’m happy to do this. _But_ that doesn’t mean you shouldn’t be punished for breaking the rule. Go to that magical little toy box of Cas’ and get something for me to tie you to the bedposts.”

Jimmy immediately rose to his feet with a grace that had Dean breathless. For the first time since he woke, Dean actually noticed that Jimmy was completely bare, his own pajama bottoms missing. What caught Dean’s eye was the tiniest flash of color between Jimmy’s round asscheeks. Dean’s hand shot out and grasped Jimmy’s arm firmly, pulled him close enough to speak with his lips brushing at the shell of Jimmy’s ear.

“What’s this?” Dean asked as he tapped the smooth base of the blue plug with his free hand.

“A plug, Sir.” Jimmy said, bit back a whimper at the stimulation.

“And what exactly were you thinking when you put this in. Were you expecting me to fuck you, pet?” Dean growled and gave the plug another sharp tap.

“I wanted to be ready for however you wanted to use me, Sir.” Jimmy said and managed to control his reaction better this time.

It took every fiber of Dean’s being to keep from throwing Jimmy down and fucking him silly at that.

“Well, guess we’ll have to see if you earn a _reward_ after your punishment.”

Dean released Jimmy’s arm, kept his eyes trained on Jimmy’s naked body as he moved over to the open armoire. Watched and tried to push down mingled excitement and nerves that built up in him. God, Jimmy was gorgeous; miles of slightly tanned bare skin, a tight, rounded ass and perfect damn thighs. Wisps of anticipation and heat flickered through Dean's belly.

Pretty quickly, Jimmy returned and held out two fur lined leather cuffs with short lengths of metal link chains attached. Dean looked them over but he couldn’t quite figure out how they were supposed to go around the post and attach, so he looked up at Castiel with a raised brow.

Castiel, as always, understood and without a word he made his way behind Jimmy to the furthest post at the foot of the bed. Curiously, Dean watched as he reached up and, much like the armoire earlier, pressed against part of a carved vine design that wrapped around the post. The small section slid up to reveal an opening. He reached around and pushed something in on the other side and a sturdy looking metal hook slid out.

Dean couldn’t help but shake his head. He was beginning to feel like he was in James Bond’s play room.

“Put them on, pet.” Dean said as he moved to the other post.

Dean's fingers skated along the mirroring vines until he felt the wood shift a little as he slid his fingers across it. He copied Castiel’s movement and pushed the piece up, exposed a duplicate hole. On the other side he found that one of the carved leaves had a little give and when he pressed firmly, the wood sank in and a hook appeared.

A little smirk ticked up the corners of Dean’s mouth as he turned back to Jimmy. The cuffs were already wrapped around his wrists and buckled, so Dean reached out and tested the fit, made sure they weren’t too tight. Satisfied, Dean tilted his head toward the foot of the bed.

“Face the bed.”

Jimmy complied instantly and Dean stepped up behind him. Ran his hands down the warm skin of his back then slid them back up to his shoulders before he skimmed both hands down his left arm. Wrapped one hand around his cuffed wrist and grabbed the chain with the other, lifted both up. He gauged about where Jimmy would be centered and hooked the chain four links in from the end. Lightly, Dean slid his hands back along Jimmy’s arm, across his shoulders, and gave his right arm the same treatment.

Jimmy had to stand on his tiptoes and stretch almost to the point of strain for Dean to hook the other chain but once it settled down into place he stood flat footed, though the muscles in his back and shoulders rippled with the pull. Uncertain if it was too much, Dean looked to Castiel, and settled at his approving nod.

Much more confident, Dean leaned in and brushed his lips against the shell of Jimmy’s ear as he whispered soft and low, “What’s your safeword, pet.”

“Chicken Little.” Jimmy responded immediately and Dean was surprised that unlike before Jimmy’s voice held no shame and Dean had no desire to laugh at the choice.

“Tell me, how many do you think you deserve for breaking my rule?” Dean asked as he picked the flogger back up and ran his fingers through the strands.

“As many as would please you, Sir.” Jimmy said, again without a moment of hesitation.

_God, he’s perfect._

Still, Dean was at a loss. He had no idea what an average person would think was a lot, nevermind someone who was used to taking much more. He looked over at Castiel and some of the helplessness must have bled through his mask of control because Castiel held up both hands, all ten fingers extended. Dean nodded and turned back to stare at Jimmy’s back.

And stare.

And stare.

It wasn’t that Dean wasn’t into this. Even if he hadn’t gotten hard from the blows he’d received he’d still have been standing at attention. His cock was rock hard, leaking and almost aching he was so painfully into it. But he couldn’t turn off the voices in his head. The ones that told him he shouldn’t, he didn’t know what he was doing, he was gonna hurt Jimmy, hurt someone he lo-.

In an instant, the voices vanished as a warm firm body pressed up against Dean’s back. Castiel’s hand rested gently on Dean’s shoulder before it glided down his arm and his fingers wrapped around Dean’s where he gripped the flogger.

“Together.” Castiel whispered into Dean’s ear and Dean’s tension melted away.

“Count for me, pet.” Dean growled as their arms drew back in tandem.

Comfortably, Dean relaxed his hand in Castiel’s firm grip.

“One!” Jimmy cried out, his voice still amazingly steady.

The swing was mostly Castiel’s doing as Dean let himself feel the speed, the strength behind the blow.

“Two.”

Dean felt the movement and his body mirrored it. By the fourth swing Dean barely even noticed Castiel’s hand on him, the pressure was so light and his focus so narrowed down to Jimmy and his state. His voice was still unwavering but Dean could see a slight tremor go through him after the last hit.

“Five.” Jimmy’s voice was softer this time.

Totally focused on Jimmy, he didn’t even notice when Castiel stepped away to watch with an admiring eye. While Jimmy’s body strained in his position and with his anticipation, it was the ripple of muscle under golden freckled skin that captured Castiel’s attention. Dean’s barely restrained strength, pulled taut by his will to keep Jimmy safe alone.

Castiel had never seen anything more beautiful than them.

“Seven.” Gasped Jimmy.

Both of them were covered with a sheen of sweat that glistened in morning light filtered through filmy curtains. Jimmy’s back and shoulders were striped and Castiel was pleased to note that there were minimal intersections and Jimmy’s vital areas had been carefully avoided.

“Ten.” Jimmy’s voice was barely more than a whisper.

“That’s it, that’s all. You’re done, sweetheart.” Dean said as he dropped the flogger to the floor and rushed to Jimmy.

Wordlessly, Castiel picked up the flogger and brought it to the armoire before he retrieved a small tub of cooling lotion.

“So good, so good pet. You did so good.” Dean murmured in Jimmy’s ear as he released the buckle on the leather cuff and carefully helped Jimmy lower it. He rubbed Jimmy's wrist with one hand and his shoulder with the other to make sure his circulation was flowing freely before doing the same to the other side.

“Lay him down on the bed in case he-” Castiel wasn’t able to finish his sentence before Jimmy’s legs gave out.

He needn’t have worried though. Dean’s reaction was instantaneous, his hands slipped beneath Jimmy’s underarms and supported him without putting any pressure on his back. He carefully lowered Jimmy so that his knees were on the edge of the bed before he silently encouraged him to lay down.

“We aren’t finished playing yet, pet, but you did so good with your punishment that I’m gonna let you take a little break.” Dean said soothingly once Jimmy was sprawled out on the rumpled bedding.

Castiel appeared at Dean’s side with a bottle of orange juice, a straw already in the open neck. Gratefully, Dean took it from Castiel’s hands and pressed the straw to Jimmy’s lips.

“Drink for me, angel.” Dean murmured.

Sweetly, Dean whispered praise as Jimmy slowly drained the bottle and Castiel rubbed cream across the marks that criss crossed his back. When both were finished Dean stood gradually and set the empty bottle down on the night stand. He let his fingers trail over the unblemished skin of Jimmy’s arm.

“Be right back, promise.” Dean said before he walked over to where Castiel stood at the end of the bed, having already returned the tub of cream to it’s home.

“You’re doing amazing, Dean.” Castiel said warmly as he reached up to cup Dean’s cheek.

Dean leaned into the touch and allowed himself to soften briefly before he firmed up his resolve again.

“I told him we weren’t done yet, but what do you think? Should we stop?” Dean spoke in hushed a whisper.

“It’s completely up to you. It was intense and it’s your first time. As far as Jimmy’s concerned though, he has a much higher tolerance for extended play when in subspace.” Castiel matched Dean’s quiet tone. “If you’re okay with continuing I can give you a few ideas, unless you’ve got something in mind?”

“Yeah, I’m good to keep going if you think Jimmy would prefer it.” Dean hesitated, his cheeks slightly flushed. “I thought… maybe… maybe I’d like to try using him as a cockwarmer? I… I read about it the other day…”

At Castiel’s beaming smile, Dean’s nerves disappeared and he quietly explained what he had in mind. When he was done Castiel nodded and left the room out through the door that led to the their common room.

Dean moved back to the bed and stretched out beside Jimmy, stroked his hair and unmarred skin. When Castiel poked his head back through the door and nodded again fifteen minutes later Dean sat up slowly and moved around the bed to stand beside Jimmy.

“Break’s over, pet. Time for breakfast. Sit up slowly and when you’re ready to stand go to the other room. Kneel on the pillow in front of the couch, facing toward it.” Dean said, the warmth his voice had held while he was caring for Jimmy earlier completely gone. “But don’t test my patience and take too long.”

Abruptly, Dean moved toward the open armoire and made a show of ignoring Jimmy to examine various objects. He watched him from the corner of his eye though and ensured that when Jimmy finally rose from the bed he was steady on his feet. Dean stalled long enough that he was sure Jimmy would be situated before he closed the armoire and headed for the other room.

Castiel had followed through on Dean’s request to a T. He sat on one of the oversized armchairs while he watched some morning news show and munched away on a plate full of fruit and pastries. There was another plate that sat on the ottoman near where Jimmy was kneeling, facing the couch in the same position as he’d been in when Dean had first woken up.

Dean’s cock, which had started to soften while he’d taken care of Jimmy, gave an interested twitch. He forced himself to will it away as he sat on the couch and his knee brushed Jimmy’s arm as he leaned forward to grab the plate. After he took a few bites of some sort of berry filled pastry, Dean picked up a bitesize chunk of melon. Without taking his eyes off the tv he reached over and pressed the juicy fruit to Jimmy’s lips.

“Eat like a good pet.” Dean said when Jimmy didn’t immediately open.

At the command Jimmy complied, leaned his head just a little forward as he opened his lips around the food and the fingers that held it. Dean shot a glare at Castiel when he heard a soft chuckle from his direction. No doubt a reaction to the way Dean’d had to shift and press down against his groin at the feel of Jimmy’s tongue while he cleaned juice from Dean’s fingers before he pulled away and chewed silently.

It took the entire half hour news program for Dean to clean his plate between himself and Jimmy. Dean wouldn’t pass a test on the content of the day’s news if he had a gun to his head though. Still, he’d done a good job of pretending if he did say so himself.

“Cas, feel like getting your ass kicked at some Halo?” Dean asked nonchalantly as Jimmy cleaned the last of the juice and crumbs from his fingers.

“In your dreams, Dean.” Castiel said with a smirk as he stood and walked over to the cabinet that housed the game systems and took out two wireless remotes.

As Castiel got the system started up Dean leaned down and placed a finger lightly under Jimmy’s chin, tilted his head up so that their eyes met.

“Now, pets don’t need to play video games but I wouldn’t want you to get bored.” Dean said with a grin. “Here’s what you’re gonna do. Your brother’s gonna come sit where you’re kneeling and you’re gonna get him nice and hard before you sink that cock hungry little ass of yours down. Then you’re gonna sit there and keep him nice and warm. No wiggling or squeezing or any other little tricks to try and make him come. Understand?”

“Yes, Sir.” Jimmy said as his eyes glazed over further.

Dean didn’t miss for a second when Jimmy’s cock started hardening.

“Just so you don’t go accidentally coming without permission I think I’ll need to make sure you’re too occupied to even consider getting off.” Dean traced Jimmy’s pink lips with his thumb as he spoke. “Besides, can’t have Castiel having all the fun. Your master might get jealous. So you’re gonna use that hot little mouth of yours to keep _my_ cock warm. I can’t be losing to your brother though so you better not distract me, pet.”

When Castiel came to stand beside Jimmy Dean looked down at him with a raised eyebrow. After a moment Jimmy scrambled out of the way. Castiel sat down on the ground, back against the couch, one shoulder pressed against Dean’s leg. For a moment the room was still.

“Now, pet.” Dean growled when Jimmy didn’t move.

The words sent him into motion. Jimmy scrambled to kneel in front of Castiel before he bent himself in half. He gripped the waistband of Castiel’s sweats and tugged them down, exposed his already hardening cock. Without any preamble Jimmy sank his lips around Castiel, right down to the root, gave him a quick and dirty deep throat.

While Jimmy worked his brother to fully hard, Dean reached around and grasped the plug between Jimmy’s cheeks. After a couple of gentle twists and tugs, Dean pulled it out which caused Jimmy to gasp around Castiel’s hot flesh.

“That’s enough pet.” Dean warned. “You’re supposed to get him hard, not off. Cas?”

Castiel nodded, reached into the pocket of his bunched up pants and pulled out a small bottle of lube. Dean gripped the hair at the back of Jimmy’s hair. He’d stopped bobbing but his mouth was still covering Castiel’s cock, and Dean yanked back. Gave Castiel room to lube up. Dean let Jimmy go and fought back a moan that wanted to break free as he watched Jimmy straddle Castiel's lap, one hand held Castiel’s cock still while he slowly sank down onto it.

Castiel, the asshole, showed no sign of being affected by the fact that he was buried in Jimmy’s hot ass, which Dean knew from experience was fucking perfect and tight. Suddenly, Dean was very glad they hadn’t bet on this game because he was pretty damn sure he was gonna be a hell of a lot more distracted than Castiel was.

He was also pretty fucking amazed that Jimmy showed equal signs of control. Without so much as a whimper or a wiggle, he sat motionless though Dean knew intimately that Jimmy loved the feeling of a cock up his ass.

It occurred to him after a moment that Castiel was looking back over his shoulder at him and Jimmy was focused on him as well. Thank fuck his brain had decided to come back online and he realized what they were waiting for.

Quickly, he scooted forward on the couch, tucked one knee between it and Castiel, then  spread the other as far as he could comfortably hold it for an extended amount of time. He shoved the waistband of his pj pants down and freed the hard on he’d been trying to get rid of. From the reading he’d done Dean knew that it was really hard for someone to keep a hard cock in their mouth, that it was better if he was soft but he was having a hard time getting that message to his cock.

It didn’t help when Jimmy pressed against Castiel, who’d wrapped his arms around him to hold the controller behind him and engulfed Dean’s cock in his mouth. Dean started thinking about anything he could, baseball, his fifth grade math teacher that smelled like mothballs and death, the look on Sammy’s face when he found out he’d have to give up the mutt he’d taken in when they moved to a complex that didn’t allow pets. All the gross, sad things he could remember in a last ditch effort to kill his boner.

To Dean’s shock, he actually began to soften after a while which helped Jimmy relax more into his position and soon he rested limp against Castiel, his head pillowed on Dean’s thigh as he kept his jaw loose. Dean was grateful that he kept his swallowing to a minimum though it meant a wet patch was forming as Jimmy drooled around Dean’s cock.

Even though Dean became accustomed to the feeling, his concentration wasn’t at all close to what it normally was and Castiel soundly handed him his ass. When Dean got tired of losing, he dropped his remote down on the couch and gently brushed the hair from Jimmy’s face, slowly so he didn’t startle him.

“You’ve done so good, pet. Why don’t you get me nice and hard again and then I’ll fuck you into the couch while Cas fucks your face… use you for what you’re good for.” Dean said. “If you’re real good, I might even let you come.”

A small whimper was the only warning that Dean had before Jimmy lifted his head and went to fucking town on his dick. Which was immediately on board with the plan and perked right the fuck up. So much so that Dean had to tighten his grip on Jimmy’s hair and stop his movements before he blew his load early.

“That’s enough.” Dean said, his voice rough.

Gently, Dean pushed Jimmy away and stood up, then hooked his hands under Jimmy’s arms. Careful not to jostle him, Dean helped him lift himself up off of Castiel’s lap. When Castiel’s cock slid free Jimmy let out a soft little gasp. For a moment Dean had second thoughts, concerned that doing anything to Jimmy’s ass might be too much but as usual Castiel seemed to read his mind.

“Poor boy, doesn’t like being empty after being full for so long.” Castiel said fondly as he helped maneuver Jimmy onto his back stretched across the couch.

Dean couldn’t help but wince at the hiss of pain Jimmy let out when his back pressed against the couch.

“Maybe… maybe this wasn’t a good idea.” Dean said softly to Castiel.

Unfortunately for Dean, Castiel decided that was a good time to make Dean figure things out on his own. For a second he hemmed and hawed but he couldn’t get over the idea of pushing on if Jimmy was in too much pain.

“Pet, I’m going to ask you something and I expect you to be completely honest. There won’t be any punishment as long as you’re honest. Got that?” Dean asked firmly.

“Yes, Sir.” Jimmy answered, his gaze glassy as he struggled to focus on Dean.

“Is this hurting your back too much? If it is we can still fill you up pet, but we’ll just do it differently. Do we need to change positions?” Dean hoped his tone left no room for anything other than the truth.

“No, Sir. This is good, Sir.” Jimmy replied before he finally relaxed fully into the soft couch with a sigh.

Dean nodded in response and slipped his sweats off. He lifted Jimmy’s outside leg and slid between Jimmy’s parted thighs to kneel on the couch. He watched as Castiel followed suit; Got naked and wiped his dick off with his pants before he tossed them to the side.

As soon as Castiel had a leg slung across Jimmy’s chest Dean pressed forward, guided his cock in to Jimmy’s slick, loosened hole. Thankfully Jimmy was well lubed from his morning prep and Castiel’s lubed cock because otherwise the spit from Jimmy’s blowjob wouldn’t have been nearly enough to slick the way and Dean was already hilted in Jimmy’s ass before he even remembered lube.

Hot and tight and so damn good, Dean withdrew and then thrusted back in harshly, filled Jimmy over and over with hard snaps of his hips that he knew were punishing. Castiel had said Jimmy liked it rough, and Dean was hellbent on giving him that.

Nothing hotter than watching Castiel’s perfect ass muscles twitch as he shallowly fucked forward into Jimmy’s mouth. Pace leisurely and a slow counterpoint to the fast, rough thrusts Dean made. Heat built rapidly in Dean’s groin, God, he’d been turned on all damn morning and there was no way he’d last all that long. Pleasure seared through him with every movement he made inside Jimmy, strung him up tight. 

God, Dean could tell that Castiel wasn’t nearly as close as he was to coming, more a testament to Castiel’s iron control than a mark against Jimmy’s mouth. Still, Dean had some strange need to finish after him, to be the one to hold onto their control.

Without thinking Dean slid his arms out from under Jimmy’s legs, let them drop to wrap around his waist, and snaked a hand up to Castiel’s ass. He heard Castiel make a startled sound seconds before he spread Castiel’s cheeks and dove in to lavish his hole with strong, quick strokes of his tongue. Dean hadn’t ever done this before and if he was honest with himself it was mostly because he wasn’t sure if he would like it. But he sure as fuck liked the sounds that were coming out of Castiel as he alternated between fucking into Jimmy’s mouth and fucking himself on Dean’s tongue.

Dean felt the moment Castiel peaked; his rim tried to clench around the tip of Dean’s slippery tongue. He pulled away quickly.

“His face.” Dean gasped. “Come on his face.”

Castiel responded immediately. Dean watched as he slid back and the fact that he could clearly hear Jimmy’s moans now meant that Castiel was no longer stuffed down Jimmy’s throat. Having achieved his goal of outlasting Castiel, Dean slipped his arms back behind Jimmy’s knees and fucked into him relentlessly as he chased his own release.

When it came, Dean barely had the wherewithal to follow through on his plan to cover Jimmy with their come. He pulled out quickly and managed to get a hand around his cock just as his orgasm hit and come streaked across Jimmy’s belly. As the last tremor of his orgasm passed, Dean reached down and circled Jimmy’s painfully swollen cock.

At the same time, Castiel slipped off of him and knelt next to the couch, covered Jimmy’s face and neck with licks and nips and sucks.

“So good for us, baby. It’s your turn now. Go ahead and let go. Come for us, pet.” Dean praised as he stroked Jimmy’s cock, slicked up from Jimmy’s precome and stray drops of Dean’s own spend.

He never thought that a degrading thing, like calling someone a pet, could sound so full of love and yet the fact that he knew how his own words sounded had him flushing. Thankfully the moment Jimmy was given permission, his body arched up and he added to the come that covered his body as he shook with the exertion of the morning.

When Dean had finished stroking Jimmy through the last of his orgasm he pushed himself up to stand on shaky legs. Castiel joined him and they both looked down at Jimmy who was completely blissed out, drenched in their combined spend and never happier.

“God, he’s beautiful.” Dean said, too awed to care about how sappy he sounded.

“Yes, he is.” Castiel said fondly, though Dean was too busy looking at Jimmy to realize that Castiel was looking at _him._ “I think that we’ve probably pushed him as far as we should today.”

“Yeah, I was thinking the same thing.” Dean nodded before he looked up at Castiel uncertainly.

Castiel caught his look and reached up to tap his neck silently. Dean nodded again and moved to kneel next to Jimmy’s head.

“Hey Jimmy, sweetheart.” Dean said softly as he smoothed Jimmy’s hair. “We’re all done. You’ve done so good for me. I’m gonna take your collar off now, if that’s okay and then we’ll get you cleaned up and tucked in for a nap. Does that sound good?”

Somehow Jimmy managed a small nod in his near unconscious state. Gingerly, Dean slid a hand beneath Jimmy’s neck and released the clasp. He rubbed the slightly reddened area he revealed when he pulled the collar free and then moved up to massage Jimmy’s jaw.

Dean and Castiel nearly had to carry Jimmy to Castiel’s ensuite bathroom as useless as his legs were. They opted on a bath and thankfully the tub had great hot water and even better pressure so the tub filled quickly. Dean cleaned the come and sweat off of Jimmy, kept his touches almost clinical while Castiel made use of the separate shower. When they were both cleaned up Dean and Castiel dried Jimmy off before they slipped clean sweats on him and tucked him into bed. After that, Castiel sent Dean off to shower while he got Jimmy to drink more juice.

Dean quickly showered and then toweled off. Didn't wanna spend too much time away from them even if the hot water had felt amazing. Seriously, he needed a shower like theirs in his life more often, the water pressure was fucking phenomenal.  

Back in the bedroom he was greeted by the sight of Jimmy and Castiel twined together, limbs nearly indistinguishable, sound asleep. Happily, Dean slipped between the sheets on the other side of Jimmy and wrapped them in his own limbs. As he drifted off, a deep sense of contentment filled him. He’d given them what they wanted and he’d done it without doing them any damage. For once he felt like he was actually able to give them as much as they gave him.


	12. Chapter 12

Monday morning Dean got to school a little later than usual thanks to Sam taking forever in the shower. Probably in retaliation for how long Dean’d taken; he’d gotten accustomed to being particularly thorough since he never knew what to expect from Jimmy and Castiel.

It’d been amazing getting to spend the week before with Jimmy and Castiel but there was still something bothering him. Something he should’ve done a million times over by then but hadn’t.

Time to fix that.

Purposefully, he walked up to Jimmy where he was leaned against his locker by himself. Only a minute before the bell was gonna ring, but Dean smirked at Jimmy and boxed him in with his forearm propped up above Jimmy’s head. His other hand settled on the side of Jimmy’s neck and he kissed him like it was going out of style, tasted the mint-bubblegum toothpaste Jimmy used and wondered briefly when he’d started to find that so sexy.

“Mornin’” Dean murmured against Jimmy’s lips and Jimmy hummed his greeting back, his hands clutched in the back of Dean’s leather jacket.

Cheeks flushed and lips shiny pink, Jimmy’s eyes were a little glazed when Dean pulled back. Dean’s smirk widened into a grin as the bell rang and just before he backed up a step and went to walk to class Dean casually said, “Love you.”

Jimmy’s blue eyes widened and the blush on his cheeks darkened. Mischievously, Dean’s eyes sparkled as he backed up. Made it all of two steps away before Jimmy pulled him back by his tie, slotted their lips together and kissed Dean like he _needed_ to.

Whispered, _“Love you so much,”_ into Dean’s mouth.

Finally he pulled back to look up at Dean. Jimmy's eyes darkened and Dean felt warm all over while Jimmy played with his tie. Couldn’t help but lean down to kiss him again but Jimmy stopped him with a hand on his chest and a lopsided little smirk.

“Later.” Jimmy said despite the fact that his blue eyes were practically lit up with desire, “Get your hot ass to class.”

Fondly, Dean rolled his eyes and a smile tugged at the corners of his lips before he walked away, “See you at lunch?”

“You bet.” Jimmy answered, and the tone of his voice sounded like a promise, sent a shiver down Dean’s back.

***

Just before the bell rang for lunch Dean’s phone vibrated in his pocket. He pulled it out and pressed the power button. The screen lit up with a single notification.

 **Jimmy:** _Meet us behind the bleachers_ _;)_

Like some kinda Pavlovian response Dean was half-hard by the time he’d finished reading the message. Could be any reason that they wanted to him to meet them there. Maybe it wasn’t sexual at all, but Dean’s body sure thought it must be. He bit his lip and shifted a little in his seat before he texted back.

 **Dean:** _k :)_

The bell rang and Dean stuffed his things into his backpack, did up the bottom couple of buttons on his blazer to help hide the chubby he was sporting, and then made his way through the mass of people that were streaming into the halls. Breathed a sigh of relief when he got to the front doors and slipped outside. He was glad it was a pretty mild day out because he hadn’t bothered to grab his leather jacket from his locker.

As he approached the bleachers he spotted Castiel and Jimmy, no one else around, weirdly. Dean was pretty sure there was generally a small crowd of stoners who perpetually hung out there. Totally empty now though, and the smirk on Jimmy’s face as Dean walked up made it abundantly clear just how intentional that was.

The two of them looked so damn hot; Jimmy casually leaned up against a metal support pole, and Castiel right next to him, eyes dark and unreadable as they watched Dean. Nervously, he licked his lips right before he got close enough to touch, smiled and was about to say hi, but before he could get it out Jimmy pulled him in for a kiss by his tie.

Lips and tongue brutally insistent, and Dean gave in readily. He was painfully hard so fast his head spun a little, and _fuck,_ it was so different to have Jimmy be demanding with him, so fucking hot.

And then against his lips Jimmy said, “God, this tie… Haven’t been able to get you and this tie outta my head since I first laid eyes on you.”

A violent burst of arousal flashed through Dean as Jimmy slid his tongue slick and perfect back into Dean’s mouth, brushed it roughly against Dean’s, so goddamn sexy while he slowly tugged Dean’s tie loose.

Dean hadn’t noticed when Castiel had moved from Jimmy’s side, but he had, because the next thing Dean knew, Castiel’s body was pressed against his back in a hard line of heat, his lips trailed plush and warm up the side of Dean’s neck, nuzzled just under his jaw and then sucked lightly there.

Felt so fucking good that it barely penetrated the fog of desire that rolled in steady waves through Dean when Castiel slid his hand down Dean’s arm to his wrist and lifted it over his head. Dean pulled back just enough to look up and watch as Castiel tied his wrist to a navy blue tie he’d already looped over the steel bar above them. Another one hung just a couple inches away.

Instantly, Dean’s eyes flashed down to Jimmy’s collar, how had he missed the fact that his tie was gone?

Castiel already had Dean’s other arm over his head and was working on knotting it securely when Dean’s brain finally kicked in again, “Hey, guys… What’s… what’s going on?”

“Cassie said I’ve been so good lately. He’s gonna give me a present.” Jimmy replied with a wide devious grin that said _you’re the present, in case you didn’t catch that._

Wordlessly, Castiel’s hands slid back down Dean’s secured arms just before Jimmy flipped up Dean’s collar, slid his loosened tie up, turned it around and guided the back into his mouth at the same time as Castiel tightened it which effectively gagged Dean. _Hot as fucking hell._

Then Castiel leaned in close to his ear, whispered, “Can’t have anyone hear you scream. And trust me when I say you won’t be able to stop yourself.”

Jimmy quickly unbuttoned Dean’s shirt and started to kiss dark marks into the skin he revealed. Paid special attention to Dean’s nipples; licked and kissed them into tight, sensitive buds while Castiel sucked his own mark just under Dean’s collar, where his neck and shoulder met. So hot that Dean’s body already felt strung tight.

Castiel’s hands slid around Dean’s waist to his belt buckle just as Jimmy dropped onto his knees in front of him. Lightly, Jimmy ran his nose along the length of Dean’s cock through his pants, and _fucking Christ._ A second later Castiel’s mouth was back right next to Dean’s ear as Jimmy repeated the movement and Castiel unbuckled his belt, “Anything happens you don’t like, or you want us to stop, just snap your fingers. We’ll be listening for it. It’s how you’ll safeword. Can you show me right now?”

Light-headed and hazy with pleasure Dean bit down on the tie in his mouth and tried to stifle the little noise that tried to work it’s way out of his chest but he did it, snapped his fingers and felt a rush of white hot pleasure when Castiel whispered, “Good boy.”

Faster than Dean’s mind could keep up, Castiel had his pants undone, pushed down along with his boxer-briefs to tangle at his ankles. There was a brief moment of mild panic when Dean realized just how exposed he was right now, outside, _at school_ for fuck’s sake, but the slight tinge of embarrassment at the thought of discovery just fueled the arousal that burned through him.

Without warning, Jimmy closed his lips around Dean’s cock and sucked him down all the way. A low moan ripped free from Dean’s chest, muffled slightly by his tie. _God, so, ah- God._

So fucking hot a moment later when Castiel sank to his knees behind him, grabbed handfuls of Dean’s ass and spread his cheeks. Licked a hot, broad stripe right over his hole before he circled it slow and wet. Sent little tingles of pleasure sparking through Dean. He spent long minutes just licking around it, until Dean was wordlessly begging with grunts and little jerks of his hips for more.

Castiel gave in and worked his tongue inside, swirled it in hot little rolls and Dean damn near lost it. Between Jimmy sucking his cock like a goddamn pornstar and Castiel eating his ass like one, there was no fucking way Dean was gonna last. When Castiel slid a spit-slick finger inside of him along with his tongue, the slight burn mixed with the ecstasy that rushed through him, pushed him hard and fast.

One particularly hard suck from Jimmy and Dean came, so fucking hard, right into Jimmy’s mouth. Spilled warm come on his tongue while Jimmy sucked him through it, slid his tongue over the head of Dean’s cock to lick up the last drops and then stood up.

So fucking sexy, Castiel didn’t even pause in what he was doing, just kept licking into Dean. Jimmy briefly pulled the tie from Dean’s mouth,  cupped the back of Dean’s neck and brushed their lips wetly together before he pushed his tongue inside. The bitter-salt taste of his own release flooded Dean’s senses as Jimmy shared it with him. _So goddamn hot._ Jimmy kissed him filthily until the taste of Dean’s come had all but faded.

The whole time, Castiel had kept up with his tongue and finger, worked Dean from oversensitive right back to desperate and needy. Dean’s cock hardened fully again when Castiel sank three lube-slick fingers into him and crooked them to find Dean’s prostate. Heat and pleasure lit Dean up, combined with the sting of being stretched that quickly and just felt so fucking _good._

“Such a good boy for us, Dean.” Castiel murmured as he watched his fingers slide in and out of Dean.

“Mmm.” Jimmy echoed, fitted the tie back into Dean's mouth and then knelt down in front of him again. “Always so good.” 

Jimmy’s hands parted Dean’s legs enough so that he could duck down and kiss Castiel between Dean’s thighs. So. Fucking. Hot. Their hair tickled Dean’s balls and ass and Dean couldn’t see what was happening but he could _hear_ it and fucking Christ it was so damn sexy.

Overwhelmed, Dean closed his eyes right before Castiel pulled back, and withdrew his fingers. Jimmy’s mouth sank hot and wet and fucking _awesome_ around Dean's cock. _Fuck._

There was a snick of a zipper and then a wet sound as Castiel slicked up his cock before he slowly pressed into him one silky inch at a time until he was all the way in. Dean sucked in sharp breaths and tried not to lose it again, because how fucking embarrassing would it be if he blew his load _twice_ before Castiel even _really_ fucked him.

And then Castiel slammed into him with quick snaps of his hips that fucking perfectly pushed Dean’s cock further into Jimmy’s mouth each time. _So good._ Dean forced his eyes open when he heard Jimmy’s zipper and he looked down to see Jimmy’s lips obscenely stretched around his cock, shiny-swollen and so fucking hot, and then lower where Jimmy had his cock fisted in his hand which jerked it at a furious pace. A little moan echoed in Jimmy’s chest, vibrated through Dean’s cock and felt fucking _amazing._

“Jimmy.” Castiel said, voice dark and low and so fucking hot, “Don’t come until Dean does.”

Jimmy groaned, and slowed his hand. Dean thought, he shouldn’t have bothered because he was already right on the edge, so fucking close. Castiel’s hands on his hips were tight, and Dean hoped they’d leave finger shaped bruises there. So turned on he could barely think, but he knew he wanted every last mark they wanted to leave on him. Wanted to be _theirs_ in every fucking way imaginable.

Dean moaned, couldn’t hold back anymore, ragged noises that sounded ripped from his lungs only barely muted by his tie. One of Castiel’s hands left his hip and covered Dean’s mouth, “It’s okay, Dean, be as loud as you want. I’ll keep you quiet.”

 _Fuck, fuck,_ God, _fu-fuck._ Dean’s sweat-slick body froze up as heat and pleasure built up feverishly in his gut. So, so close. A hard rock of Castiel’s hips into him on just the right angle shoved Dean’s cock far enough into Jimmy’s mouth that it bumped the back of his throat. Jimmy moaned and Dean came in hot spurts, euphoric.

Jimmy groaned hotly, sped up his hand while he sucked every last bit of Dean’s come into his mouth and came with this sexy little whimper that Dean wanted seared into his brain.

“Fuck, that was hot.” Castiel said heatedly.

Harder, Castiel fucked into Dean, faster, so fucking hot, Dean goddamn loved being fucked after he’d come. Loved the way he could focus on how Castiel felt inside him, so hard and big and perfect. Wasn’t all that long until Castiel pushed deep into Dean, his hips stuttered and he came in hot splashes inside him.

Felt so good that Dean groaned, and rocked back onto his cock. With a slow kiss to Dean’s neck, Castiel gradually withdrew.

“Lick him clean.” Castiel told Jimmy.

Jimmy’s cheeks heated faintly, but he complied. Crawled behind Dean and lapped up the come that’d leaked down the back of his thighs before he slipped his tongue inside to chase the rest. _Fuck,_ Dean was half-hard again between how it felt as Jimmy licked and sucked at his hole, and the way Castiel came around in front of him to kiss him slow and lazy through it.

Eventually though, Jimmy pulled back and said, “Think I got it all.”

Castiel smiled against Dean’s lips and replied, “Good. Pull up his underwear and pants. Much as I’d love to try for one more,” he pointedly looked down at Dean’s dick, “lunch is nearly over and I think it would be more beneficial if we got some food into us.”

Weakly, Dean nodded in agreement, and Castiel kissed him once more before he untied his wrists and retrieved their ties, a little worse for wear, but not like the teachers were gonna say anything to them about it.

They dressed and straightened themselves up. Dean pulled Jimmy into his side, tucked him under his arm and couldn’t help but grin down at him as Jimmy looked up at him with love shining in his eyes. Castiel took Jimmy’s other side, his hand wrapped around Jimmy’s back and he reached to hook his pointer finger into Dean’s back pocket.

Dean couldn’t resist dipping down as they walked mostly blind past the garage that housed the team buses and captured Jimmy’s lips in another kiss. He could hear a slick slide and knew that Castiel was teasing the space just below the hinge of Jimmy’s jaw which always made Jimmy practically purr.

“Dean?”

For a second Dean froze when the familiar voice called out. His lips still pressed to Jimmy’s, his tongue still in a mouth not his own. Then, slowly, his mind came back online and he pulled away from Jimmy’s mouth, though his hand gripped tighter at the material on Jimmy’s back. As much as he didn’t want to, Dean turned to face the person who’d called out to him.

“Dad… what are you doing here?” Dean asked in an attempt to put off the inevitable.

Dean felt Castiel’s finger leave his pocket and a quick glance from his peripheral vision showed that he’d also moved a little away from Jimmy too. As if it wasn’t too late to explain this away. As if Jimmy wasn’t still tucked under Dean’s arm.

Dad stood there staring at Dean while his face started to redden, eyes filled with shock and something else. Something that looked a lot like revulsion. Something hard knotted up inside Dean as his worst fear unfolded before him.

“I had to do some work on the swim team’s bus. They got a meet tonight a few towns over and it’s been acting up.” Dad said as he wiped his hands on a greasy rag. Suddenly had a hard time looking at them. “Boys, why don’t you get on to class now. I gotta have a chat with my son.”

When neither of them moved to go, Dad’s eyes narrowed down. Dean had no doubt that if they stayed Dad would say whatever it was he was planning to say, audience or not. He couldn’t stand the thought of them witnessing it, though.

“Go on, guys. I’ll see you in class later.” Dean said softly, his eyes on Dad.

“Dean…” Jimmy almost whimpered and they both hesitated.

He turned to look at them and hoped the smile he gave them after he kissed Jimmy gently on his head didn’t look too forced. That the loud, panicked beating of his heart wasn't audible to anyone but him.

“It’s fine. Go. I’ll be okay.” Dean said, then gave Jimmy a reassuring squeeze before he extricated himself from the partial embrace and stepped away.

After another moment of hesitation they turned and walked toward the school. To their credit they only looked back once.

As soon as they turned a corner and were out of view Dean faced his father. It took every ounce of strength Dean had to move toward him. Dad had never laid a hand on either him or Sam but Dean’d also never seen him filled with so much anger and whatever that other look he couldn’t place in his eyes was.

He came to a dead stop a couple of feet away and shoved his hands into his pockets, looked down at his scuffed school required shoes.

“Somethin’ you wanna tell me son?” Dad’s voice was low and dangerous.

Anger welled up inside Dean. Everything he’d done all his life for Dad, always doing what he was told and _now_ Dad was gonna look down on him for being who he was? _Bullshit._

“Yeah, Dad. I like boys. A lot. Still like girls too but right now I’m pretty content with dick. Oh and before you get any idea that I might not be _that_ gay, I take it up the ass. Regularly.” Dean gritted out, felt a sick enjoyment at the look of shock that flashed across his father’s face.

“Jesus Dean.” Dad said as he raked a hand through his hair.

Defiantly, Dean crossed his arms and levelled a stare at Dad that clearly telegraphed how much he didn’t care what he thought. Dad stood there with his mouth agape and shook his head.

“You think I give a flying fuck about you being gay or bi or whatever?” Dad asked, and for a moment something a lot like hurt flashed across his face. “It’s the twenty first century.”

Suddenly, Dean found himself lost as words he’d spoken so long ago in a bar to two amped up pricks were echoed back at him.

“All I care about is that you’re happy.” Dad said, some of the anger in his voice faded. “But I got eyes, Dean. They’re _brothers_. You think I didn’t see what was happening? That’s… that’s _wrong!”_

“Dad-”

“Do their parents know?” Dad cut Dean off.

All of a sudden Dean’s previous confidence vanished. It felt like the ground was shifting beneath him and he just couldn’t quite find his footing.

“No… Dad… you can’t… please.” Dean started pleading, ready to fall to his knees and beg if necessary.

“Dean, you can’t ask me to keep quiet. If it were you and Sam-” Dad said with the same twist of disgust coloring his words.

“Dad, it’s not. And it’s not the same. This isn’t some older sibling tricking their kid brother or sister into doing things they don’t understand. This isn’t a parent abusing their child. Please Dad. They love each other. They love me.” Dean hesitated briefly, “And I love _them.”_

“C’mon, Dean you _can’t_ know that. You’re just a kid. You’ve only known them what, a _couple of months?”_ Dad said with a shake of his head.

“Not much younger than you and Mom were. And you always told us you knew within minutes that you’d love Mom for the rest of your life. Are you saying that wasn’t true?” Dean asked as he pointedly moved to catch John’s gaze.

“That’s not the same Dean.” Dad growled.

“You’re right, it’s not. ‘Cause we were friends first. And then it still took me more than a month to realize that… that I love them. I’ve never felt this way before, Dad, and _not_ for lack of partners. I’m not saying that this is absolutely it for the rest of my life. I can’t possibly know that. But I’d _like_ it to be. They make each other better. They make _me_ better.” Dean drew in a breath. “They make me happy. Didn’t you just say that’s all you wanted for me?”

Slowly, Dean watched the last of the fight drain from Dad’s face and his shoulders slumped.

“You’re making it hard on yourself son. You think society’s gonna make life easy on you? Three people in a relationship? Brothers? Not like you can go necking at the movies or couple skate at the ice rink.” Dad said, still frowning.

Dean couldn’t help but laugh.

“Dad, for one? This isn’t the seventies or whatever when you were dating mom. We don’t do that kinda thing. For another, we make it work. Doesn’t hurt that they have more money than God and can pay for people’s discretion. But it _is_ kinda sad when that isn’t the case. Seeing two people so in love have to hide it because of what other people think. Please don’t be the kinda person they have to hide from Dad.” Dean implored.

He could tell he was making ground but there was still something that held his dad back.

“Dean… what if… Sounds like they’ve been together for a while. Plus they have something more than just romantic love. What if one day they decide that they’re enough for each other? I don’t wanna see you get hurt, Son.” Dad said and reached out for the first time, gripped Dean’s shoulder.

“I get it Dad.” Dean said with a small grin. “I’ve asked ‘em the same damn things before and they make sure I know they feel just as much for me as they do for each other. But, really, even if one day they do decide to leave me? I wouldn’t give up a second I’ve got with them to avoid that. Would you have given up a second with Mom? If you knew how much you were gonna hurt when you lost her?”

“No, Son.” Dad said softly. “Not even a second.”

Dad pulled Dean in for a crushing hug and held him there.

“You tell those boys I’ve got a shotgun and access to some grease removing chemicals that’ll make a human body disappear.” Dad said gruffly.

Dean pulled away laughing.

“Their parents said basically the same thing to me.”

“Oh really, _their_ parent’s knew about you and _I_ had to catch you in the act.” Dad said with a raised brow.

“Yeah, believe me, Dad that wasn’t something I decided. I almost crapped myself when Cas announced at the dinner table that I was their boyfriend.” Dean said, as a smile crossed his face at the fond memory.

“Well, you better get your butt to class, Dean. And no ditching to make out. You think I haven’t noticed that this is the longest I’ve gone without getting a phone call about you skipping class or not doing your work? Whatever else, those boys seem to be a good influence. Make sure they stay that way.” Dad said before he headed back into the garage.

When Dean met up with the twins for History, fear burned bright in their eyes. He wasted no time at all, walked up and pulled them in for a tight hug, then kissed both of their foreheads.

“We’re good.” Dean said as he pulled away, wanted to stave off their fears quickly.

“Yeah?” Jimmy hesitantly asked.

“Yeah. Dad just really wants me to be happy. If what we have is that, he’s not gonna make waves. And it is. I’ve never been as happy as when I’m with you guys. I love you. No matter what, you never have to worry about that. Got it?”

Dean waited until he received twin nods before he released them and moved to take his seat.

And it was true. He was happy. Now that the one thing that’d been hanging over his head was gone, he could really see a life with them. A happy one. Some day he’d wake up every morning to the most beautiful pairs of loving blue eyes he’d ever seen and _damn_ he just couldn’t wait.


	13. Epilogue

Sluggishly, Dean picked up the last box from the back of the u-haul. He really, _really_ regretted his decision to put his foot down when Castiel had said they’d just hire a moving company to bring their things to campus. _No, it’s part of the experience,_ Dean had insisted.

Stupid was what it was. They’d had to park a block away behind all the _other_ people who’d gotten there earlier, and while Dean only had a couple boxes of things, Castiel’s _books_ alone had been several trips to the car. Add to that their clothes, toys, and the stuff Jimmy had picked out to decorate their room with, and yeah, hell of alot of trips, and a very sweaty grumpy Dean.

Thank fuck this was the last trip. Like a good boyfriend, Dean’d told them he’d grab the last load while they relaxed. Honestly, Dean was still kinda shocked he’d gotten in at all. Once Jimmy and Castiel had convinced him it’d be worth it, Dean had worked damn hard (with their help) to nail the rest of his classes. Even wrote a kickass essay about how growing up he’d had to help raise his little brother after his mom died.

And sure, maybe a little birdie might’ve whispered into someone’s ear how happy the Novak’s would be if their son’s friend got into the same school as them, but after a lifetime of hard knocks, Dean was glad to have something go well… Besides the best mid-year transfer ever.

Funny that up until this year, Dean never woulda thought of going off to university and leaving Sam alone with Dad. Things had changed so drastically for all of them though, they were in a good place, happy. Sam and Dad had started getting along better, and yeah, Dean might still worry a bit, but both of them had made it clear that they’d be fine and couldn’t wait to see him on his first break.

Plus Sam had a whole network of friends to rely on, and it wasn’t like they were half-way across the country or something. They were just a few hours away, and Sam knew all he had to do was call, and Dean would be there. He was confident it wouldn’t come to that though, hopefully.

When Dean got through the crowded lobby, past the keycard access door to the elevators, into a crowded elevator and finally off at their floor, the last thing he expected to find when he walked into their three bedroom suite was Castiel reclined on the couch, head rested against the arm of it with Jimmy straddling his lap. And yet, there they were, lips locked as Jimmy rode his cock.

The box in Dean’s hands fell to the floor and narrowly missed landing on his toes. Jimmy didn’t even pause at the sudden noise, just kept right on going.

“Jesus, guys.” Dean groaned, zero to sixty in the span of a few seconds, his cock strained the front of his faded jeans.

“Dean,” Jimmy breathed into Castiel’s mouth, so fucking sexy.

“Jeez, I was only gone like ten minutes.” Dean grumbled, already too hot in his skin as he walked over, kicked off his shoes on his way and got his clothes off.

“Wanted,” Jimmy gasped like Castiel had hit exactly the right spot when he thrusted up, “Wanted to give you a show.”

“Mmm.” Castiel agreed, “For being so good.”

“Fuck,” Dean said, low and hot.

And Christ, they were beautiful together, just an unreal amount of gorgeous. Perfect slim defined bodies covered in sweat, eyes hooded and dark. The way their bodies fit together, like they were made for this, and fuck, they really were, Dean thought fervently.

“Come stand behind me.” Castiel demanded when Dean went to sit in the armchair across from the couch so that he could watch.

Dean raised an eyebrow, but hesitated, “I’m kinda gross and sweaty from hauling in our stuff. You don’t want me over there.”

“Yes, we do.” Jimmy insisted, didn’t break his stride, but did shift so he could look at Dean hungrily. “Besides, don’t know if you’ve noticed but I fuckin’ love the way you smell.”

“Yeah, but-”

“Dean, _now.”_ Castiel said harshly, and Dean immediately obeyed.

Fisted his cock as he stalked closer to them. Stopped with his thighs against the arm of the couch, just behind Castiel’s head. Fluidly, Castiel shifted them so that his knees were bent, feet planted on the cushions, and Jimmy was pushed further up his body, able to reach Dean.

“Suck his cock.” Castiel said, and Jimmy instantly threw himself into it.

Jimmy wrapped his lips around Dean’s cock with a moan and sucked like he was paid to. Dean’s hands slipped through Jimmy’s hair, ran down the back of his neck and over his shoulders before they slid back up into his hair.

Pleasure built hard and fast in Dean, every slick slide of Jimmy’s lips pushed him higher. All heat and suction and Dean loved every second of it. Castiel grabbed Jimmy by his hair. Stopped him from moving.

“Fuck his face.”

 _God,_ the groan Jimmy let out at those words was frantic and hot and Dean didn’t even think, he just thrusted forward and back, over and over, and Jimmy sucked in desperate breaths when he could. So fucking sexy, tears gathered in the corners of Jimmy’s eyes, his body suspended in a frozen tableau of pleasure. Then he let out a guttural moan and shook between Dean and Castiel, came messily onto Castiel’s chest.

“Fuck, so hot, Jimmy.” Dean groaned, pushed his cock into Jimmy’s mouth hard a few more times until the heat in his belly shattered.

He came in hot splashes down Jimmy’s throat, roughly grunted, “Jimmy, Cas, ah, fuck.”

Let Jimmy suck the last drops up, and then pulled out. Spent, but still turned the fuck on while he watched Jimmy kiss Castiel, saw a flash of white on Jimmy’s tongue and knew Jimmy was pushing his come into Castiel’s mouth.

Castiel moaned low and urgent, pushed desperately up into Jimmy and ground his hips there as he came. Spent, Dean knelt down next to the couch and soothingly ran his hands along Jimmy’s back and up Castiel’s arm until Castiel finally collapsed back against the couch with a shuddering breath.

“Well that was a hell of a way to celebrate moving in together.” Dean said tiredly.

“Mmm.” Castiel agreed.

Jimmy yawned and laid down more fully on Castiel before he answered, “Can we just do that everyday? Fuck classes. Let’s just spend the next few weeks holed up in here.”

“I’m good with that.” Dean said, completely drained.

Exasperated, Castiel rolled his eyes, “No. We’re going to class on Monday and before then everything needs to be organized in here.” Jimmy whined but Castiel continued on like he hadn’t heard him, “We need to figure out sleeping arrangements, and hookup our laptops. Arrange the rest of the things we brought and we need to test if the door is strong enough for our over the door restraints.”

“That last one sounds fun.” Dean said cautiously.

“Doesn’t it?” Castiel asked, “That’s why I saved it for last. Once the other stuff is done, we can test it.”

“Aww.” Jimmy pouted, “I don’t even wanna _move_ right now, Cassie.”

“Yes, well, _I_ don’t want to be covered in dried semen. We all need to take showers, then we’ll get started.” Castiel said.

“Too bad the shower can’t fit all of us at once.” Jimmy lamented, “Maybe next year we should think about an apartment.”

“Or a house.” Castiel suggested.

Dean just sat there and let them make their plans. He’d learned by then to pick his battles, and that he needed to stop feeling insecure about them spending money on him, because it was gonna happen either way, and everyone felt a whole lot better if he didn’t get bent out of shape over it. Bit of an adjustment for him to go from next to dirt poor to being taken care of, and there were still times when he bucked at it, but he was learning.

The best thing about being with Jimmy and Castiel was that they were learning too, all of them were growing together, and committed to figuring themselves and each other out. Part of that was letting Jimmy and Castiel do nice things for him, or all of them, and part of it was them sacrificing the finer things now and then to make Dean comfortable.

As he sat on the floor and listened to them, Dean just felt extremely grateful that this was his life, that this is where everything he’d gone through had led. Because right there, with Jimmy and Castiel, well, it might not be perfect, nothing in life ever was, but it was perfect for _him._

**Notes for the Chapter:**

> Thanks so much for reading everyone. <3 We'd love to hear what you thought of our fic in the comments or over on Tumblr [@DaydreamDestiel](http://daydreamdestiel.tumblr.com) and [@spnbrennafae](http://spnbrennafae.tumblr.com). <3


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